A Guide to Organophosphorus Chemistry [illustrated] 0471318248, 9780471318248

Table of contents :
L ..............8
M ..............35
THE COMMON 3cooHDINATE FUNCTIONS orº A ..............44
C ..............56
and Inorganic Syntheses ..............93
and Inorganic Syntheses ..............132
5 ..............139
and Inorganic Syntheses ..............166

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Organophosphorus Chemistry

Volume 22

A Specialist Periodical Report

Organophosphorus Chemistry Volume 22

A Review of the Recent Literature Published between July 1 9 8 9 and June 1 9 9 0 Senior Reporters

D. W. Allen, Sheffield City Polytechnic B. J. Walker, Department of Chemistry, David Keir Building, The Queen's University of Belfast

Reporters

C. W. Allen, University of Vermont, U.S.A. R. Cosstick, University of Liverpool 0. Dahl, University of Copenhagen, Denmark R. S. Edmundson, formerly of University of Bradford C. D. Hall, King's College, London

ISBN 0-85 186-206-3 lSSN 0306-07 13 Copyright @ 1991 The Royal Society of Chemistry A II Rights Reserved N o part ofthis book mu?)be reproduced or transmitted in an-vform or by any rnecins - graphic. electronic: including photocopying, recording tqjing. or irlformution storage and retrieval systems - without written

pcwnission .from The Rqval Society of Chernistn

Published by The Royal Society of Chemistry, Thomas Graham House, The Science Park, Cambridge CB4 4WF Printed in Great Britain by Billing & Sons Ltd.. Worcester

Introduction

Volume 22 introduces one of us, David Allen, as a new Senior Reporter, although not as an author since David has contributed to Organophosphorus Chemistry since volume 7. David replaces John Hobbs, who we thank for all his hard work, not only as Senior reporter but also as author of the "Nucleotides and Nucleic Acids" chapter. We have been fortunate in persuading Rick Cosstick to take on the formidable task of writing this chapter and we welcome him. Unfortunately we have again not been able to include the "Physical Methods" chapter but we hope to do so next year. A highlight of the year covered by this volume was the XIth International Conference on Phosphorus Chemistry held in Tallinn, Estonia, during July 1989. This was not only an unusual and most enjoyable experience, it was also a most timely venue in view of the far reaching developments in Eastern Europe. We met many old, and made many new, friends and it is clear that the traditional strength of organophosphorus chemistry in the USSR is safe in the hands of excellent young chemists with modern ideas. We look forward to the XIIth International Conference at Toulouse in 1992. As measured by the numbers of publications the activity in all the areas covered has increased. The interest in the px-bonded area has increased again after last year's apparent decline. The results of a structural study of bis(bory1)diphosphines indicate a P-P bond length in the range normally reserved for P=P bonds. This suggests that the P-P bond shortening in diphosphenes, which has always been interpreted as being due to 3px-3px, may to some extent be a consequence of rehybridization. There have been a number of developments worthy of special mention in chemistry invoIving pentaco-ordinated compounds and intermediates. These include reports of molecular mechanics calculations to study the hydrolysis of cyclic phosphorus esters, further detailed studies of the reactions of tervalent phosphorus compounds with acetylene carboxylates and the first synthesis of a pentaco-ordinated phosphorus compound containing a three-membered (phosphirene) ring. There has also been further elegant work in the area of phosphatrane chemistry. Novel phosphine oxide cage compounds have been prepared from tris(4-hydroxypheny1)phosphine oxide and their structures have been determined by X-ray crystallography. High temperature thermolysis of

vi

lntroduction

dimethylphosphins oxide gives 2-phosphapropene via elimination of water; this is perhaps surpesing since it involves loss of the P=O bond. In tervalent phosphorus acid chemistry the main area of activity has again been the use of tervalent phosphorus acid derivatives for the preparation of phosphates or modified phosphates of biochemical interest. Apart from the nucleotide field, (vide infra), pentavalent phosphorus acid chemistry seems to be mainly in the doldrums; exceptions to this are the areas of myo-inositol phosphate and aminoalkylphosphonate chemistry where activity remains high. It is gratifying to observe that the nucleotide field continues to produce a large quantity of innovative phosphorus chemistry. The potential use of anti-sense oligonucleotides to control gene expression is now widely accepted and has been responsible for the explosive increase of activity in the synthesis of modified oligonucleotides. However, if the anti-sense therapeutic principle is going to fulfil its initial expectations and maintain momentum, exciting and widely reproducible biological activity will have to be demonstrated in the near future. Activity also remains high in the synthesis of non-radiolabelled oligonucleotides for use as hybridization probes. Many versatile procedures have been reported in the last year which enable oligonucleotides to be labelled with multiple reporter groups either during automated chemical synthesis or as a post-synthesis modification. Reports of the use in synthesis of the Wittig reaction, and the related methods involving phosphonate and phosphine oxide carbanions and iminophosphoranes, have, if anything, increased and many of these include useful innovations. New results and speculation on the mechanism of the Wittig reaction continue to be published by groups with well established reputations in the area. Activity in the phosphazene area has increased over that reported in volume 21 as indicated by an increase of fifty-five in the number of citations. Three particular areas deserve special mention. These are the use of the aza-Wittig reaction in the construction of heterocyclic rings, the structural diversity and solvent selectivity in macrocycles formed by reactions of long chain diamines (or oxodiamines) with N3P3C16 and lastly the synthesis of new heterophosphazene polymers by ring opening reactions of cyclic he terophosphazenes. D W Allen and B J Walker

Contents

CHAPTER

1

Phosphines and Phosphonium Salts By D.W. Allen

1

Phosphines

1

1.1 Preparation

1

1.1.1

From Halogenophosphines and Organometallic Reagents From Metallated Phosphines By Addition of P-H to Unsaturated Compounds By Reduction Miscellaneous Methods

1.1.2 1.1.3 1.1.4 1.1.5

2

7 7 9

1.2 Reactions

12

1.2.1 1.2.2 1.2.3 1.2.4

12 12 13 15

Nucleophilic Attack at Carbon Nucleophilic Attack at Halogen Nucleophilic Attack at Other Atoms Miscellaneous Reactions

Halogenophosphines

16

2.1 Preparation 2.2 Reactions

16 17

Phosphonium Salts

19

3.1 Preparation 3.2 Reactions

19 21

4

p,-Bonded

23

5

Phosphirenes, Phospholes and Phosphinines

30

References

34

3

CHAPTER

1 3

2

Phosphorus Compounds

Pentaco-ordinated and Hexaco-ordinated Compounds By C.D. Hall Introduction

48

Structure, Bonding and Ligand Reorganization

48

Acyclic Phosphoranes

50

Ring Containing Phosphoranes

53

4.1 Monocyclic Phosphoranes 4.2 Eicyclic and Tricyclic Phosphoranes

53 59

...

Contents

Vlll

5

CHAPTER

CHAPTER

3

63

References

69

Phosphine Oxide and Related Compounds By B.J. Walker Preparation of Acyclic Phosphine Oxides

71

Preparation of Cyclic Phosphine Oxides

71

Structure and Physical Aspects

74

Reactions at Phosphorus

77

Reactions at the Side-Chain

77

Phosphine Oxide Complexes

82

References

85

4

Tervalent Phosphorus Acids By 0. D a h l

1

Introduction

87

2

Nucleophillc Reactions

87

2.1 Attack on Saturated Carbon 2.2 Attack on Unsaturated Carbon 2.3 Attack on Nitrogen, Chalcogen, or Halogen

87 89 89

Electrophilic Reactions

92

3.1 Preparation 3.2 Mechanistic Studies 3.3 Use for Nucleotide, Sugar Phosphate, Phospholipid or Phosphoprotein Synthesis 3.4 Miscellaneous

92 95 95 103

Reactions involving Two-co-ordinating Phosphorus

106

Miscellaneous Reactions

106

References

110

3

4

5

CHAPTER

Hexaco-ordinated Phosphorus Compounds

5

Quinquevalent Phosphorus Acids By R.S. Edmundson

1

Phosphoric Acids and their Derivatives

114

1.1 Synthesis 1.2 Reactions 1.3 Uses of Phosphoric Acid Derivatives

114 128 133

Phosphonic and Phosphinic Acids and their Derivatives

134

2.1 Synthesis 2.2 Reactions

134 161

References

174

2

cot1ter1ts

CHAPTER

ix 6

Nucleotides and Nucleic Acids By R . Cosstick

1

Introduction

181

L

Mononucleotides

181

2.1 Nucleoside Acyclic Phosphates 2.2 Nucleoside Cyclic Phosphates

181 185

3

Nucleoside Polyphosphates

187

4

Oligo- and Poly-nucleotides

189

4.1 DNA Synthesis 4.2 RNA Synthesis 4.3 Oligonucleotides Containing Modified Phosphodiester Linkages 4.4 Oligonucleotides Containing Modified Sugars 4.5 Oligonucleotides Containing Modified Bases

189 199

5

217 223

Oligonucleotide Labelling, Conjugation and Affinity Studies

226

6

Cleavage and Sequencing Studies

234

7

Interaction of DNA with Metals and Small Molecules

238

Analytical and Physical Studies

241

References

244

8

CHAPTER

205

7

Ylides and Related Compounds By B.J. Walker

1

Introduction

252

2

Methylenephosphoranes

252

2.1 Preparation and Structure 2.2 Reactions of Methylenephosphoranes

252 254

2.2.1 2.2.2 2.2.3 2.2.4

Aldehydes Ketones Ylides Co-ordinated to Metals Miscellaneous Reactions

254 259 262 262

3

Reactions of Phosphonate Anions

269

4

Selected Applications in Synthesis

276

4.1 Carotenolds, Retenolds and Pheromones 4.2 Leukotrienes, Prostaglandins and Related Compounds 4.3 Macrolides and Related Compounds 4.4 Nitrogen Heterocycles 4.5 Miscellaneous Reactions

276 276 280 282 282

References

292

Contents

X

CHAPTER

8

Phosphazenes By C.W. Allen

1

Introduction

298

2

Acyclic Phosphazenes

298

3

Cyclophosphazenes

305

4

Cyclophospha(th1a)zenes and Related Compounds

312

5

Miscellaneous Phosphazene Containing Ring Systems Including Metallophosphazenes

315

6

Poly(pho8phazenes)

318

7

Molecular Structure of Phosphazenes

327

References

332

AUTHOR INDEX

343

Abbreviations

AIBN C IDNP CNDO CP DAD DBN DBU DCC DIOP DMF DMSO DMTr EDTA E.H.T. ENU FID g.1.c.-m.8. HMPT h.p.1.c. i.r. L.F.E.R. MIND0 MMTr MO MS-C1 MS-nt MS-tet NBS n.q.r. p.e. PPA SCF TBDMS TDAP TFAA Tf ,O THF Thf ThP TIPS t.1.c. TPS-C1 TPS-nt TPS tet TsOH

-

U.V.

*

bisazoisobutyronitrile Chemically Induced Dynamic Nuclear Polarization Complete Neglect of Differential Overlap cyclopentadienyl diethyl azodicarboxylate 1,5-diazabicyclo[4.3.O]non-5-ene 1,5-diazabicyclo[5.4.O]undec-5-ene dicyclohexylcarbodi-imide [(2,2-dimethyl-1,3-dioxolan-4,5-diyl)bis-(methylene)] bis(dipheny1phosphine) dimethylformamide dimethyl sulphoxide 4,4'-dimethoxytrityl ethylenediaminetetra-acetic acid Extended Huckle Treatment N-ethyl-N-nitrosourea Free Induction Decay gas-liquid chromatography-mass spectrometry hexamethylphosphortriamide high-performance liquid chromatography infrared Linear Free-Energy Relationship Modified Intermediate Neglect of Differential Overlap 4-monomethoxytrityl Molecular Orbital mesitylenesulphonyl chloride mesitylenesulphonyl 3-nitro-1,2,4-triazole mesitylenesulphonyltetrazole N-bromosuccinimide nuclear quadrupole resonance photoelectron polyphosphoric acid Self-consistent Field t-butyldimethylsilyl tris(diethy1amino)phosphine trifluoroacetic acid trifluoromethaneaulphonic anhydride Tetrahydrofuran 2-tetrahydrofuranyl 2-tetrahydropyranyl

tetraisopropyldisiloxanyl thin-layer chromatography tri-isopropylbenzenesulphonyl chloride tri-isopropylbenzenesulphonyl-3-nitro-l,2,4-tr~azole tri-isopropylbenzenesulphonyltetrazole toluene-p-aulphonic acid ultraviolet

Abbreviations used in Chapter 6 are detailed in Biochem. J., 1970,120, 449 and 1978,171,l

1 Phosphines and Phosphonium Salts BY D. W. ALLEN

1

PhosDhines

..

.-

rom HalOaenODhOSDhlneS and Oraanometallic Reaaenta Grignard procedures have been used to prepare phosphines bearing up to two adamantyl- or l-adamantylmethyl- substituents at phosphorus. Organolithium reagents nevertheless remain the reagents of choice in phosphine synthesis. Selective metallation of pendant thienyl groups of copolymers of 2-vinylthiophen and divinylbenzene, followed by treatment with chlorodiphenylphosphine, has given a polymer-bound heteroarylphosphine which has been used as a co-reagent in the halogenation of alcohols.2 Direct wmetallation of arylethers has been employed in the synthesis of the acyclic polyetherphosphine (l), the phosphonium salts derived therefrom giving high &-selectivities in Wittig reactions under salt-free conditions. A range of phosphines bearing bulky organolithium alkenyl substituents ( 2 ) has been prepared reagents generated by direct metallation at carbon adjacent to silicon.4 Metallation of imines at carbon alpha to the imino group has led to the synthesis of the functionalised phosphines Sequential trans( 3 ) , together with other products.5'6 metallation of 1,l'-bis(tributylstanny1)ferrocene with butyllithium has enabled the synthesis of new diphosphinoferrocenes ( 4 ) , and further examples of chiral ferrocenylphosphines, e. 9., ( 5 ) ,a have been prepared by nuclear lithiation of chiral aminoalkylferrocenes Direct followed by treatment with chlorodiphenylphosphine. metallation at the benzylic carbon of the 2,2'-dimethylbiphenyl system is the key step in the synthesis of a series of bidentate phosphines, e.g. , ( 6 ) l o Halogen-metal exchange of chiral 2,2'-diiodo-6,6'-dimethylbiphenyl with butyllithium has given a chiral diorganolithium reagent which, on treatment with

.

chlorodiphenylphosphine, provides the stable, chiral diphosphine (7).l1 In contrast, an earlier report12 that the reaction of

chlorodiphenylphosphine with 2,2'-dilithiobiphenyl yields the 1

Organophosphorus Chmrstrv

Me\

P

SiMe3 I

R’ R ~ -CH P

(3) R’ = Prior BU

I

CH=CHSiMe3

R2 = H or Me R3 = But or C6Hll

(2) R’,R2 = Ph or NMe2 CH(R)NMe2

VPPh2 &PPh2

&PR2

( 5 ) R = menthyl

Ph

(16) n = 1-3

P. “CPh2 PCI,

I

Cp2Ti=/t-Ph

PhP*Ph

I:

Phosphiries utid Phosphotiiurii Solts

diphosphine ( 8 ) has now been shown to be in serious error, the principal products being 5-phenyldibenzophosphole (9) and triphenylphosphine.l 3 Also of concern is a report that the repetition of the literature preparation14 of the trisheteroarylphosphine (10) (admittedly with minor modifications), leads to the the phosphinic acid ( 1 1 ) . l5 Organolithium isolation of reagents derived from O-protected phenols have been employed in the synthesis of the phosphines (12) bearing sterically-crowded phenolic substituents.l6 Lithiation at nitrogen of the pyridylamino-phosphine (13), followed by treatment with chlorodiphenylphosphine, has given the chelating diphosphine (14).17 Several reports have appeared of the application of unusual organometallic reagents in phosphine synthesis. Treatment of 2-lithiopyridine with anhydrous zinc chloride results in the formation of a 2-pyridylzinc reagent which can be used to introduce the 2-pyridyl group at phosphorus in a controlled manner. Thus, e.g., in its reaction with phenyldichlorophosphine, the 2-pyridyl(pheny1)chlorophosphine (15) is formed. This has then been converted the phosphide route into a new class of binucleating ligands ( 16). l 8 The sterically crowded dichlorophosphine ( 17) (accessible from the reaction of phosphorus trichloride with lithium diphenyl(2-pyridy1)methanide) is converted into the thermally stable phosphirane (18) on treatment with calcium, strontium or barium cyclooctatetraenide.l9 The reaction of phenyldichlorophosphine with the readily accessible titanacycle (19) affords a convenient route to the phosphetene (20).2o

a

3.1.2 2 .- The reactions of metallophosphide reagents with alkyl halides and sulphonate esters continue to be widely employed in the synthesis of new phosphine ligands, many of which are chiral and have obvious potential in homogeneous catalysis. Chiral substrates derived from simple carbohydrates have been used in the synthesis of chiral diphosphines, 1-23 e.g . , ( 21 ) ,23 although in some cases yields are poor due to elimination reactions. Among new chiral systems prepared using lithiophosphide reagents are the diphosphines (22),24 ( 2 3 1 and ~ ~ (24),26 the latter having a "natural bite" angle of 120", and able to occupy diequatorial positions in trigonal bipyramidal complexes. New optically-active di- and tri-phosphines, e.g., (25), have been prepared from optically pure lactones and carboxylic acids via intermediate tosylatee.2 7

>( PPh2

(25)

n

0. O”,l

,NH N(CH2CH2PPh2),

Ph2P

(219), (220) --> (221), and (222) -> (223) + (224).205 The migration of a benzyl group (indeed of any group other than phenyl) has been observed for the first time in Lossen-like rearrangements of H-phosphinoylated Q-sulphonylhydroxylamines, although the process occurs less readily than that for aryl groups directly bonded to phosphoryl phosphorus. With methoxide or ethoxide the phosphinic amide (225) yields only 25-35% of the rearrangement product (226), the main products being the ester (227; R = Me or Et) and the amide (228), but with isopropoxide or tert-butoxide, the rearrangement product (226) accounts for 70-80% of the total reaction yield. The use of tert-butylamine as base leads t o (229). rearrangement, in the present instance, is of mechanistic

The

significance since it demonstrates that the migration can be based

5: Quinquevalent Phosphorus Acids

165

0

-

II O/ ,

(Et0)2PCH-CCIBut

0

I1

0

II

(Et0)2PCHCICOB~t

0

II

Ph2PNHOPPh2

L

OR 0=PCx

I

CF&HCIN=CHPh

(233)

CF3CH=NCHP h

.OR 0=PCx

120-1300c_ CF,CH,N=CPh

1

(235)

(234)

0=P(OR1),

1

P

CF&H N=CH Ph

(238)

I hh

upon an sp3 carbon and that the new N-C bond can be formed without the involvement of r, electrons.206 Methoxide acts upon (230) causing degradation, but following treatment with tert-butoxide (230) undergoes rearrangement to the mixed anhydride (231), and although this was not isolable, it was characterized following its preparation by an alternative route. Under the same experimental conditions, the corresponding methanesulphonyl derivative afforded (232) in almost quantitative yield (a 5% yield was experienced from the phosphinoyl derivative). 207 C-Phosphorylation of the imidoyl halide (233) by reaction with dialkyl fluorophosphite results in the formation of the rearrangement product (234; X = F) which, at a higher temperature, rearranges prototropically and irreversibly to the phosphonate (235; R1 = Et or Pri) On the other hand, the ester (234; X = OR1 = OPri) rearranges rather more slowly than the diethyl (236), ester at the same temperature. The tautomer of (233), reacts with trialkyl phosphite (R1 = Pr' or Me3Si) to give (237) initially which rearranges irreversibly under the reaction conditions to give (238; R1 = Prl or Me3Si). 208 The esters (239), obtained analogously, are isolable, and are quite stable at 209 room temperature, but at higher temperatures, also rearrange, the corresponding trimethylsilyl esters particularly easily.210 In the last case, an even higher temperature results in phosphoryl migration thus affording the phosphonate (240). In a series of papers Chinese authors have reported on (a) the effects of changes in solvent on the hydrolysis of a series of 2-propyl- and 2-isopropyl-l ,3,2-dioxaphospholane 2-oxides,211 (b) a theoretical treatment, by molecular mechanics, of the hydrolysis of alkylphosphonic estes and alkylphosphonic dichlorides,212 and (c) a similar treatment of substituent effects in the alkaline hydrolysis of esters of alkylphosphonic and dialkylphosphinic acids.213 In respect of the last two studies, it was concluded that using steric constants derived from work on carbon compounds led to poor correlations. However, the steric effects of substituents on rates of hydrolysis correlated well with the quantity A A E, representing the difference, calculated by molecular mechanics, between the energies of the tetracoordinate ground state of the substrate and of

.

a.

5:

Quinquevalent Phosphorus Acids

7 Bu'C=NCH~P~

O = (OR),

167

160-1 70 "C

O =r;(OR),

BdCHN=CHPh

(239)

I

R = MesSi 160 "C

O=P(OSiMe3)2

I

BdCHN=CHPh

180-200

OC-

O=P(OSiMe3), I ButCH=NCHPh (240)

Ho;k

0

II

0

(241) a; R = Ph, X = Y = CH2 b; R = Ph, X = 0, Y = CH2 C; R = P h , X = Y = O d; R = Et, X = Y = CH2 e; R = Et, X = 0, Y = CH2

HO

(242a)

(242)

(EtO)(MeO)P(O)Ph

(EtO)(MeS)P(O)Ph

(247)

(246) EtO, p+S Ph' 'SMe

0

the transition state - assumed to possess pentacoordinate geometry. In (b), the correlation was good for branched chain alkyl groups, but less S O for unbranched alkyl groups, presumably because steric effects then play a reduced part in the overall substituent effect. The results of a study of conformational preferences on the rates of alkaline hydrolysis of the diphenyl and diethyl phosphonic esters (241)214 follows the appearance, last year, of those of a similar study on diphenylphosphinic esters. A mechanism involving both penta- and hexa-coordinate intermediates has been proposed to account for the asymmetric induction (1-14%) achieved during the displacement reactions from the racemic MePhP(0)X (X = F, C1, CN, OC6H4N02-4) by alcohols in the presence of resolved forms of 1-phenylethylamine, N,N-dimethyl-1-phenylethylamine, or nicotine.215 The structures of the various cyclic and acyclic products obtained through 1,2- and 2,3- additions, both E and Z, of sulphenyl halides to dialkyl (1,2-alkadiene)phosphonates have been verified by 216 chromatographic and n.m.r. spectroscopic studies. Some reactions of 1,2-oxaphosphol-3-ene 2-oxides have been reported. When brominated under free radical conditions, 3,5-di-tert-butyl-l,2-oxaphosphol-3-ene 2-oxide (242) gave the extremely labile 5-bromo derivative (242; R = Br) which, with MeOH, gave the 5-methoxy derivative. The 2,5-dihydroxy compound was obtained by hydrolysis; its reaction with diazomethane gave dimethyl 8-(2,2,6,6- tetramethyl-3-oxohept-4-en-5-yl)phosphonate indicating a tautomeric equilibrium between the cyclic (242; R = OH) and acyclic (242;a) structures for the acid. The methyl ester of (242; R = MeO) undergoes slow ring opening in the presence of base, a feature immediately reversed on neutralization, and the same compound is inert to methoxy exchange except in the presence of excess HBr at an elevated temperature.217 The inability of (1,2-propadienyl)phosphonic acids (243; R1 = ~2 = OH, R4, R~ = H or alkyl) to form 1,2-oxaphosphol-3-ene 2-oxides under the influence of concentrated acids has been attributed to the failure to produce stable ‘tertiary’ cations of type (244;a; E = H). On the other hand, those phosphonic acids which would be predicted to form stable carbocations, e.g. R4 and R5 are alkyl, react readily, presumably then because of steric

5:

Quinquevalent Phosphorus Acids

169

resistance within the carbocation to rotation to (244;b). Since cyclization of compounds other than free acids occurs with electrophiles other than H+, the possibility of cations of type (244;c) cannot be excluded when E = H. A recent development is the catalysis of cyclization, by Ag+, of allenephosphonic acids which can provide only a secondary carbocation i.e. either R4 or R5 is alkyl, but not both. The cyclization of phenylpropadienylphosphinic acid is similarly catalyzed by Ag+. From the practical standpoint, the catalysis enables the cyclizations to be achieved in hours at room temperature rather than over even more extended periods at l o o o . 218

Dialkyl (2-methylamino-1-propeny1)phosphonates exist as the enamine tautomer in CC14 solution, but are acylated to give the B-acyl derivatives. 219 Competitive displacement of the Me0 and MeS ligands from Q,S-dimethyl phenylphosphonothioate, when the latter is treated with NaOEt in EtOH, results in the formation of p-ethyl S-methyl phenylphosphonothioate (246) and preferentially, Q-ethyl Q-methyl phenylphosphonate (247), both with inversion of configuration; each displacement is accompanied by racemization resulting from simultaneous and competitive displacement of EtO groups. Further displacements by EtO- lead, in each case, to diethyl phenylphosphonate. The racemization of (246) is 22 times faster than that of (247), whilst the displacement of MeS from (246) is 65 times faster than the displacement of Me0 from (247). The conclusion reached was that the displacement of MeS does not occur Y k i an inversion pathway simply because a retention pathway, as recorded in 220 earlier literature, is blocked energetically. In another study, reactions of the ( € 3 ) p ( 3 ) p , - ( mixed +) anhydride (248) were examined.221 For each of (a) alkaline methanolysis, (b) acidic methanolysis, (c) alkaline hydrolysis, and (d) ammonolysis, displacement occurred preferentially at the phenyl-phosphonyl centre with inversion of configuration. The treatment of (248) with KSH (followed by MeI) yielded racemic Q-ethyl S-methyl phenylphosphono- dithioate (249) by attack at the phosphonyl phosphorus, together with (B)-(-)-Q,S-dimethyl Q-PhenYl phosphorodithioate (250) by attack at the phosphoryl phosphorus. Q-Ethyl (B)-phenylphosphonochloridothioate (251) and (B)-Q-ethyl

PhBu'P(S)OSO2CF3

[Bu'PhP=S]+[C F,SO,]-

(254)

PhBu'P( X)OSiMePh (C OH7- 1)

(255) x2

-

(256)

But\ 00 /p\+ R S-Me

>k

X-

-

x2

-x2

.p

But\ /p\+ Fc SMe X3-

>:

(257) a; R = Ph

But,+

X

P ' R' \SMe

Scheme 18

5: Quinquevalent Phosphorus Acids

171

Q-phenyl phosphorochloridothioate (252) were each obtained when (248) was acted upon by Pel5; here, inversion still predominated although the extent of racemization was greater than that found for the alcoholysis and hydrolysis reactions. The displacements were considered in terms of pentacoordinate intermediates. The behaviour of tert-butylphenylphosphinothioic chloride towards Ag’ contrasts markedly with that of the corresponding iodide. In MeN02, the chloride is unreactive, but the iodide affords a mixture of phosphorus-containing products. Tert-butylphenylphosphine sulphide was notable in its absence. The phosphine sulphide (253) was obtained when the reaction involving the iodide was carried out in anisole. Both the iodide, preparable from the mixed anhydride (254), and the latter itself, react with MeOH-Ag+ to give Q-methyl tert-butylphenylphosphinothioate with configurational inversion. The mixed anhydride (254), which also furnished (253) in anisole, was considered, mechanistically, as reacting through structure (255). 222 Such results are in contrast to those obtained during a study of displacement reactions involving the compounds (256; X = l.p., 0, S , or Se). Attack by 0, S , N, or C nucleophiles is directed essentially at silicon rather than at phosphorus, and yet the course of the reactions depends on X , proceeding with predominant configurational retention at Si for X = 1.p. or 0, but with 223 predominant inversion when X = S or Se. A very detailed study (Scheme 18) of the bromination and iodination of the S-methyl phosphinothioate esters (257) has been reported using mainly spectroscopic techniques, but accompanied by gc/ms methods and chemical isolation.224 (Work on the chlorination of the same esters was reported earlier; see ‘Organophosphorus 170.) Both phosphonium and sulphonium Chemistry’, 1988, u, intermediates are involved extensively in the scheme. For X = I, the first part of the Scheme is displaced towards the starting materials. The reactions between (257; a and b) and iodine or bromine (the latter being the faster) are slow, both halogens being weakly nucleophilic, and reaction content studies were extended over 489 days for X = I, and for up to 56 days for X = Br. The main products obtained from (257; a) and I2 were (258;a), (260:a) and (261;a).12 but the phosphinic iodide (263;a) was not formed. Using

/

\

- 2 [R2PS2] Scheme 19

S P

5:

Quinquevalent Phosphorus Acids

I73

bromine, the bromides (263; a) and b ) were both obtained., The stereochemical course of the sequence, investigated using ester (257;a) is naturally of particular interest. When halogenation involves sulphonium salts, as in the sequence (257) --> adduct --> (258)/(259) -> (263), the outcome is one of inversion. When the favoured reaction is (258)/(259) --> (260) -> (263) + (257), the net stereochemical outcome for (263) is configurational retention because of double concurrent inversions in the reactions between (257;a) and (258;a) and between ( X - ) and (260;a), and these proposals explain satisfactorily the experimental facts although the configurations at the P atoms in (260) have not yet been confirmed. The configuration of each phosphorus atom in (261;a) can be established by direct synthesis. Thus, ( R ) - ( + ) - (257;a) with bromine gave almost racemic

-

(263) + (-1 (2611, the (B)p(s)(s)p(o) stereoisomer being the main component. Considerable racemization occurred in the reactions between (257) and bromine leading to (263; X = Br), a feature explained by the formation of the latter two routes, namely,

a

+

(258) -> (260) + (263), and (259) --> (263). N.m.r. spectroscopic evidence has been provided to suggest the dissociation of relatively simple lt3,2,4-dithiadiphosphetane 2,4-disulphides (i.e. those with non-bulky groups) in solution: this (257)

evidence comprises the observed inversion at one of the phosphorus atoms (i.e. &/trans interconversion) and the exchange reactions occurring on admixture of two symmetrical compounds (Scheme 19) .225 An X-ray examination of the product from the interaction of (2~,4~,5~)-(-)-3,4-dimethyl-2-phenyl-1,3,2-oxazaphospho1id~ne 2-oxide with an aryl Grignard reagent has demonstrated that ring opening occurs with retention of configuration at phosphorus in accord with Inch's work, but at variance with that of Koizumi, and also in stereochemical opposition to that displayed by acyclic analogues (Mislow). Acid catalyzed alcoholysis of the acyclic phosphinic amide product yields alkyl esters of arylphenylphosphinic acids with high e.e. 226

I74

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2,

I

112,

111,

19,

I

S,

I

_

S,

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.

~

ZCO,

178

Organophosphorus C'hemisrty

135. Heine, J. and Roeschenthaler, G. V., Chem.-Ztg., 1989, 113, 186. 136. Ovchinnikov, V. V., Safina, Yu. G., Cherkasov, R. A., Karataeva, F. Kh., and Pudovik, A. N., J. Gen. Chem. USSR, 1988, 58, 1841. 137. Francke, R. and Roeschenthaler, G. V., Chem.-Ztg., 1989, 113, 115. 138. El-Manouni, D., Leroux, Y., and Burgada, R . , Phosphorus, Sulfur, Silicon, Relat. Elem., 1989, 42, 73. 139. Prishchenko, A. A., Livantsov, M. V., Boganova, N. V., and Lutsenko, I. F., J. Gen. Chem. USSR, 1988, 58, 1932. 140. Bulpin, A., Masson, S., and Sene, A., Tetrahedron Lett., 1990, 31, 1151. 141. Bulpin, A., Masson, S., and Sene, A., Tetrahedron Lett., 1989, 30, 3415. 142. Iyer, R . P., Phillips, L. R., Biddle, J. A., Thakker, D. R., Egan, W., Aoki, S., and Mitsuya, H., Tetrahedron Lett., 1989, 30, 7141. 143. Hong, S., Chang, K., Ku, B., and Oh, D. Y., Tetrahedron Lett., 1989, 30, 3307. 144. zeckmann, R. K., Walters, M. A., and Koyano, H., Tetrahedron Lett., 1989, 0 , 4787. 145. Haelters, J. P., Corbel, B., and Sturtz, G., Phosphorus, Sulfur, Silicon, Relat. Elem., 1989, 42, 85. 146. Gloer, K. B., Calogeropoulou, T., Jackson, J. A., and Wiemer, D. F., J. Org. Chem., 1990, 55, 2842. 147. Jackson, J.A., Hammond, G. B., and Wiemer, D. F., J. Org. Chem., 1989, 54, 4750. 148. Hidaka, T., Seto, H., and Imai, S., J. Amer. Chem. SOC., 1989, 111,8012. 149. McQueney, M.S., Lee, S., Bowman, E., Mariano, P. S., Dunaway-Mariano, D., J. Amer. Chem. SOC., 1989, 111. 6885. 150. Yuan, C., Yuan, Q., and Xie, X., Youji Huaxue, 1989, 2, 136; Chem. Abstr., 1989, 111, 232995. 151. Kudzinx. H., Mokrzan, J., and Skowron/ska, R . , Phosphorus, Sulfur, Silicon, Relat. Elem., 1989, 2 , 41. 1567. 152. Ha, H-J., Nam, G.-S., and Park, K. P., Tetrahedron Lett., 1990, 1, 153. Elhaddadi, M., Jacquier, R., Petrus, F., and Petrus, C., Phosphorus, Sulfur, Silicon, Relat. Elem., 1989, 45, 161. 154. Soroka, M., Liebigs Ann. Chem., 1990, 331. 155. Krzyzanowska, B. A d Pilichowska, S., Pol. J. Chem., 1988, 62, 165. 156. Yuan, C., Wang, G., and Chen, S., Synthesis, 1990, 522. 157. Kudzin, Z.H. and Majchrzak, M. W., J. Organomet. Chem., 1989, 376, 245. 158. Coutrot, P., Elgadi, A., and Grison, C., Heterocycles, 1989, 28, 1179. 159. Genet, J.P., Uziel, J., Touzin, A.M., and Juge, S., Synthesis, 1990, 41. 160. Cho, S. K. and Kim, Y . J., Tachan Hwahakhoe Chi, 1989, 33, 257; Chem. Abstr., 1990, 112, 35997. 161. Sting, M. and Steglich, W., Synthesis, 1990, 132. 162. Stranin, B. P. and Khizbullin, F. F., J. Gen. Chem. USSR, 1988, 58, 1992. 163. Charandabi, M. R. M. D., Ettel, M. L., Kaushik, M. P., Huffman, J.H., and Morse, K. W., Phosphorus,Sulfur, Silicon, Relat. Elem., 1989, 2 , 223. 164. Xu, Y., Jiang, X., and Yuan, C., Synthesis, 1990, 427. 165. Karimov, K. R., Shakhidoyatov, Kh. M., and Alovitdinov, A. B., J. Gen. Chem. USSR, 1989, 59, 904. 166. Gubnitskaya, E. S., and Peresypkina, L. P., J. Gen.Chem.USSR, 1989, 59, 492. 167. Wasielewski, C., Topolski, M., and Domkowski, L., J. Praktische Chem., 1989, 331, 507. 168. van d e r l e i n , P. A . M., Dreef, C. E., van der Marel, G. A., and Van Boom, J. H., Tetrahedron Lett., 1989, 30, 5473. 169. Maier, L. and Diel, P. J., Phosphorus, Sulfur, Silicon, Relat. Elem., 1989, 45, 165. 170. ChakroGrty, P. K., Greenlee, W. J., Parsons, W.H., Patchett, A. A., Combs, P., Roth, A., Busch, R. D., and Mellin, T. N., J. Med. Chem., 1989, 32, 1886.

171. Walker, D. M., McDonald, J. F., Franz, J. E., and Legusch, E. W . , J. Chem. SOC. Perkin Trans. 1, 1990, 659. 172. bnstein, P. L., Org. Prep. Proced. I n t . , 1988, 20, 371.

5: Quinquevalent Phosp h ~ n i As c'ids

179

173. Bigge, C. F., Drummond, J. T., and Johnson, G., Tetrahedron Lett., 1989, 30, 7013. 174. Egge. C. F., Drummond, J. T., Johnson, G., Malone, T., Probert, A. W., Marcoux, F. W., Coughenour, L. L., and Brahce, L. J., J. Med. Chem., 1989, 32, 1580. 175. Hutchinson, A. J., Williams, M., Angst, C.. de Jesus, R., Blanchard, L . , Jackson, R . H., Wilusz, E.J., Murphy, D. E., Bernard, P. S., Schneider, L., Cambell, T., Guida, W., and Sills, M. A., J. Med. Chem., 1989, 32, 2171. 176. Bigge, C. F., Hays, S. J., Novak, P. M., Drummond, J. T., Johnson, G., and Bobovski, T. P., Tetrahedron Lett., 1989, 0 , 5193. 177. Kabachnik, M. I. and Polikarpov, Yu. M., J. Gen. Chem. USSR, 1988, 1729. 178. Kawashfma, T., Kojima, S., and Inamoto, N., Chem. Lett., 1989, 849. 179. Lopusinski, A., Luczak, and Michalski, J., J. Chem. Soc.Chem. Commun., 1989, 1694. 180. Quin, L. D . , Osman, F. H., Day, R. 0 . . Hughes, A. N., Wu, X. P., and Wang, L. Q., New. J. Chem., 1989, 13, 375. 181. Quin, L. D., Osman, F. H., Sadanani, N. D., Hughes, A. N., and Day, R. O., Phosphorus, Sulfur, Silicon, Relat. Elem.. 1989, 41, 297. 182. Yousif, N. M., Phosphorus, Sulfur, Silicon, Relat. Elem., 1989, 44, 249. 183. Liorber, B. G., Pavlov, V. A . , Khamatova, Z. M., Musin, R . Z., Chernova, A. V., Zyablikova, T. A., and Il'yasov, A. V., J. Gen. Chem. USSR, 1989, 59, 94. 184. Gvikova, Z. S., Kabachnik, M. M., and Lutsenko, I. F., J. Gen. Chem. USSR, 1988, 58, 1809. 185. Chen. R. and Cheng, L . , Phosphor 193; Chen, R. and Cheng, L . , Sci. China, Ser. B, 1989, 32, 1300; Chem.Abstr. 1990, 112, 235438. 186. Chen, R. and Bao, R., Synthesis, 1989, 618; 1990, 137. 187. Kulagowski, J. J., Tetrahedron Lett., 1989, 30, 3869. 188. Kim, C. U., Misco, P. F., Luh, B. Y., and Martin, J. C., Tetrahedron Lett., 1990, 31, 3257. 189. Bronson, J. J., Ghazzouli, I., Hitchcock, M. J. M., Webb, R. R., and Martin, J. C., J. Med. Chem., 1989, 32, 1457. 190. Kim, C. U., Luh, B. Y., Misco, P. F., Bronson, J. J., Hitchcock, M. J. M., Ghazzouli, I., and Martin, J. C., J. Med. Chem., 1990, 33, 1207. 191. Barton, D. H. R., Gero, S. D . , Quichet-Sire, B., and Samadi, M., J. Chem. SOC. Chem. Commun., 1989, 1000. 192. Holy, A. and Rosenberg, I., Nucleosides Nucleotides, 1988 (19891, 8, 673. 193. Krolevets, A. A., Popov, A. G., and Adamov, A. V., J. Gen. Chem.USSR, 1988, 58, 2189. 194. MondesEa, D., Tancheva, C., and Angelov, C., Chem. Ber., 1990, 123, 1231. 195. Sedqui, A., Lakhlifi, T., Laude, B., and Amaudrut, J., Bull. SOC. Chim. Belg.. 1989, 98, 865. 196. Nakazawa, H., Matsuoka, Y., Yamaguchi, H., Kuroiwa, T., Miyoshi, K., and Yoneda, H., Organometallics, 1989, 8, 2272. 197. Buzykin, V. I., Sokolov, M. P., and Ivanova, V. N., J. Gen. Chem.USSR, 1989, 59, 631. 198. Sokolov, M. P., Mavrin, G. V., Gazizov, I. G., Ivanova, V. N., and Zyablikova, T. A . , J. Gen. Chem. USSR, 1989, 59, 45. 199. Seyden-Penne, J., Bull. SOC. Chim. Fr., 1988, 238. 200. Koch, P., Rumpel, H., Sutter, P., and Weiss, C. D., Phosphorus, Sulfur, Silicon, Relat. Elem., 1989, 44, 75. 201. Breuer, E., Karaman, R., Gibson, D., and Goldblum, A., Phosphorus, Sulfur, Silicon, Relat. Elem., 1989, 41, 433. 202. K a u s h i l C h e m . Ind.(London), 1989, 389. 203. Khristov, V. and Angelov, Kh., Dokl. Bolg. Akad. Nauk., 1988, 41, 73; Chem. Abstr., 1989, 111,194873. 204. Dhawan, B. and Redmore, D., J. Chem. Res.(S), 1990, 184. 205. R abov B. V., Ionin, B. I., and Petrov, A.A., J. Gen. Chem. USSR, 1989, 55, 233. 206. Harger, M.J.P. and Smith, A., J. Chem. Soc.Perkin Trans.1, 1990, 1447.

z,

Organophosphorus Chemistry

180

207. Harger, M. J. P., Tetrahedron Lett., 1990, 31, 1451. 208. Onys'ko, P. P., Kim, T. V., and Kiseleva, E . I., J. Gen. Chem. USSR, 1989, 2, 1123. 209. Onys'ko, P. P., Kim, T. V., Kiseleva, E. I., and Sinitsa, A. D., J. Gen. Chem. USSR, 1989, 2, 1129. 210. Onys'ko, P. P., Kim, T. V., Kiseleva, E . M . , Povolotskii, M . I . , and Sinitsa, A. D., J. Gen. Chem. USSR, 1989, 2, 1496. 211. Liao, X . , Li, S., and Yuan, C., Phosphorus, Sulfur, Silicon, Relat.Elem., 1989, 42, 53. 212. Li, S., Liao, X . , and Yuan, C., J. Phys. Org. Chem., 1989, 2, 146. 48. 213. Yuan, C., Li, S., and Liao, X . , J. Phys. Org. Chem., 1990, 214. Koole, L. H., Olders, E. A. T. A., Opresnik, M., and Buck, H. M., Rsc. Trav. Chim., 1990, 109, 55. 215. Weidert, P. J., Geyer, E., and Homer, L., Phosphorus, Sulfur, Silicon, Relat. Elm., 1989, 44, 255. 216. Mondeshka, D. M., Tancheva, C. N., Angelov, C. M . , and Spasov, S. L., Phosphorus, Sulfur, Silicon, Relat. Elem., 1989, 2, 61. 217. Rardon, D. and Macomber, R. S., 218. Mualla, M. and Macomber, R. S., Synth. Commun., 1989, 2,1997. 219. Sakhibullina, V. G., Polezhaeva, N. A., Bagoutdinova, D. A., and Arbuzov, B. A., J. Gen. Chem.USSR, 1989, 59, 865. 220. DeBruin, K.E., Tand, C. W., Johnson, D. M . , and Wilde, R. L., J. h e r . Chem. SOC., 1989, 111, 5871. 221. Tang, C., Tand, Y . , and C h e T R . , Sci. Sin., Ser. B.(Engl. Edn.), 1988, 31, 649; Chem. Abstr., 1989, 111,174214. 222. zrzypczyhki, Z . , J. Phys. Org. Chem., 1990, 3, 23, 35. 223. Wozniak, L., Cypryk, M., Chojnowski, J., and Lanneau, G., Tetrahedron, 1989, 45, 4403. 224. Gawlecka, B. and Wojna-Tadeueisk,, E., J. Chem.Soc. Perkin Trans. 2, 1990, 301. 225. Ohms, G., Grossmann, G., Buchta, B., and Treichler, A., 2 . Chem., 1989, 29, 138; Ohms, G., Treichler, A., and Grossmann, G., Phosphorus, Sulfur, Silicon Relat. Elem., 1989, 45, 95. Russell, M . J. H., Tetrahedron, 1990, 46, 226. Brown, M . , Carey, J. V., 4677.

-

i.

6

Nucleotides and Nucleic Acids BY R. COSSTICK AND A. M. COSSTICK

1.

Introduction

Whilst DNA synthesis has not yet reached perfection and automated RNA synthesis is still far from routine, much of the recent effort in chemical laboratories

has

oligonucleotides.

been

directed

Undoubtedly

towards

it has

the

been

the

synthesis

modified

of

potential rewards

of

the

anti-sense approach to the control of gene expression that has stimulated this work and the explosion of papers in this area is best exemplified by reference to oligonucleotides containing phosphorodithioate linkages.

Prior to 1989 only

three comrmnications on these analogues had appeared vet in the subsequent 18 months the total number has swelled to almost 20.

A number of novel and

interesting internucleotide linkages have been prepared, many of which do not contain phosphorus and there

is one report of a stable linkage in which

manganese is directly bonded to phosphorus. A plethora of methods are now available for labelling oligonucleotide probes for hybridisation experiments. Many of these procedures are compatible with automated DNA synthesis and the introduction of multiple reporter groups provides a means of amplifying the signal from the probe. A long awaited text book on the chemistry and molecular biology of nucleic acids has

appeared'

and

major

recent developments have

been

reviewed in

symposium reports.2 2 . Mononucleotides

2.1

Nucleoside

Acyclic

Phosphates.

2-Chloro-2,4-dioxo-3-methyltetrahydro-

3,2-As-thiazaphosphole (1) has been used as a programned phosphorylating agent in

a

one-pot

synthesis

of

dithymidine

5'-~-dimethoxytrityl-2'-deoxythymidine

with

monophosphate.3'4

(1)

in

pyridine

Reaction

of

gives

the

intermediate thiazaphosphole ( 2 ) which can be opened with cleavage of the phosphorus-nitrogen bond by 3'-~-acetyl-2'-deoxythymidine in the presence of a nucleophilic catalyst. The resulting phosphorothiolate triester ( 3 ) is readily deprotected using

a

solution of

aqueous

iodine.

The

transformation of

3'-fluoronucleosides into their 5'-monophosphates has been accomplished using whole cells of the bacteria Erwinia herbicola and 4-nitrophenyl phosphate as a phosphate donor.'

Additionally, convt rsion of

the monophosphates to

the

triphosphates has also been achieved enzymatically using cells of Saccharomyces

181

I X’

Tro TrovTh ?

HO-PI

OH OAc

(3)

HO

OH (4) 0

“

O

V

T 0

h

Y

OAc

(5)

6: Nucleotides and Nucleic A c i k cerevisiae.

183

The enzymatic synthesis of nucleoside 5'-phosphates labelled with

carbon-14 or tritium has been reviewed.6 Adenosine

5'-g-monophosphate has

E-1-oxide (4) (53% yield) solution at pH 8 . 0 . 7

been

using potassium

oxidised

to

the

corresponding

hydrogen persulphate in aqueous

Interestingly, this oxidation can also be performed on

poly(rA) to give a polymer which is about 60% modified.

It is noteworthy that

the enzymatic digestion of the modified polymer is about 20 times slower than that of poly(rA).

The influence of sugar and base substituents on the stability

of the N-glycosyl bond towards acid catalysed hydrolysis of nucleosides and nucleotides has been reviewed.'

Nucleoside 5 ' -

and 3'-phosphates are both

hydrolysed at a slower rate than the parent nucleoside and this effect is chiefly attributed to conformational changes in the sugar ring, A

trinucleoside monophosphate (5) has

been

prepared

in 96% yield

by

phosphorylation of 5'-G-trityl-2'-deoxythymidine with salicylchlorophosphine (6) and

subsequent

treatment with

excess

3'-~-acety1-2'-deo~ythymidine.~The

continuing search for effective anti-viral agents has maintained the interest in the synthesis and study of nucleotide triester analogues as potential pro-drugs. A series of novel bis(nucleosid-5'-yl)phosphate

triesters have been prepared

based on 9 - [ (2-hydroxyethoxy)methyl]guanine (acyclovir) (7) and (E)-5-(2-bromovinyl)-2' -deoxyuridine (BVDU) ( 8 ) and their ability to release the biologically active nucleotides has been examined in vivo."

The lability of the aryl group

(R) to hydrolysis can be modulated by varying the substituent on the phenyl ring and at pH 7.7 a convenient rate of hydrolysis (half-life 1 7 hours) was observed for the 4-(methylsulphony1)phenyl esters.

The resulting dinucleoside diesters

are substrates for phosphodiesterases and enzymatic hydrolysis produces the nucleoside and

nucleoside 5'-monophosphate.

Toxicity studies on the BVDU

analogue suggests that BVDUMP is released after the compound has penetrated into the cell.

A range of phosphate triester analogues of the anti-viral nucleosides

9-0-D-arabinofuranosyladenine"

(9)

(=-A)

9-~-D-arabinofuranosylcytosine1z(=-C)

and

the

anti-cancer

drug

(10) have been prepared by reaction of

the unprotected nucleosides with the appropriate dialkylphosphorochloridates. Both sets of compounds are highly resistant to hydrolysis at physiological pH, but show

& vitro activity that was directly related to the lipophilicity.

These results suggest that cellular penetration by the phosphate triesters is followed by intracellular hydrolysis, by an unspecified mechanism, to the free nucleoside

(P-0-nucleoside cleavage) or

dialkylphosphinate derivatives of %-A unprotected nucleoside with

the

nucleoside 5'-phosphate.

The

(11) were prepared by reaction of the

dialkylphosphinic ch10rides.l~

These compounds

still retain a significant inhibitory effect on DNA synthesis even though they cannot serve as a source of =-AMP.

But since the activity is reduced in

Organophosphorus Chemistry

184

OR

R

OH (11) R = Bu", BzI

OH (9) B = adenin-9-yl; R = Et, Pr", Bun, n-C~H11 (10) B = cytosin-1-yl; R = Me, Et, Pr", Bun,n-C5H11

t

HO-P-0 HO i

0-Gua

TGu HO

HO

'i7

OS02Me

(EtO),-P-0

0

0

II

OCNPh2

HO (18)

comparison to the phosphate triesters ( 9 ) ,

the latter compounds would appear to

be acting by release of both the free nucleoside and nucleotide. A

stereoselective

synthesis

of

a

phosphonate

AZT 5'-monophosphate has been accomplished."'

(12)

isostere

of

The bulky t-butyldiphenylsilyl

group was used to protect the 3'-hydroxy group of the uronic acid derived from 2'-deoxythymidine (13).

A key step in the synthesis involves the generation of

the 4'-radical and subsequent reaction with diethylvinylphosphonate gives the nucleoside phosphonate ( 1 4 ) as a single diastereoisomer. The stereospecificity of the conversion is controlled by the bulk of 3'-protecting group which dictates that

reaction occurs at

the upper

9-[(1,3-Dihydroxy-2-propoxy)methyl]guanine

anti-herpes agent that is

face of

the

sugar

radical.

(DHPG) (15) is a potent and selective

known to exert its biological effect following

conversion to the monophosphate by HSV thymidine kinase.

Phosphonate analogues

of DHPG are therefore potential pro-drugs against viruses that do not specify

their own thymidine kinase.

(~)-9-[4-Hydroxy-3-(phosphonomethoxy)butyl]guanine

(16) has been prepared by alkylation of the mesylate ( 1 7 ) with the sodium salt of 2-amin0-6-chloropurine.~~ The final product is obtained after elaboration of

the

heterocycle and

cytomegalovirus.

deprotection, and

shows

potent

activity

against

A closely related isostere (18) has been synthesised through

the intermediacy of the enol ether (19).16

Conversion to the epoxide. in situ

reaction with dimethylhydroxymethylphosphonate and deprotection gives (18). variety

of

N-[2-(phosphonylethoxy)ethyl]

pyrimidine bases have

been

prepared

derivatives

(20)

of

purine

A

and

from 2-chloroethoxyethylphosphonate by

reaction with the sodium salts of heterocyclic bases.17

Deprotection of the

resulting diethyl esters was achieved with trimethylsilyl bromide.

The chemical

synthesis of phosphonate analogues of acyclic nucleotides has been reviewed.'* An

unusual

dephosphorylation

reaction

has

been

observed

in

which

a

phosphorylated 1',2'-seconucleoside ( 2 1 ) was converted to a tetrahydrofuranyl derivative ( 2 2 ) in 78% yield under transfer hydrogenation conditions.lg Papers which report the synthesis of dinucleoside monophosphates or their analogues as model studies for oligonucleotide synthesis are covered in section

4. 2.2

Nucleoside Cyclic Phosphates.

Neutral derivatives of nucleoside cyclic

3',5'-phosphates have proved to be useful probes in the study of enzyme active site mapping and as possible anti-tumour and anti-viral agents. A potentially straightforward route

to

cyclic

phosphoramidates from

hexamethylphosphorus

triamide has been reexamined.20 The reaction gives yields of up to 77% with a variety

of

5-substituted-2'-deoxyribonucleosides

and

the

intermediate

phosphoramidites can be converted to a range of cyclic phosphate analogues. The

Organophosphorus Chemistry

186

HO

OH

(25) n = 1, 2, 3

HO

OH (26)

Me2N

HO (27) B = adenin-9-yl (28) B = guanin-9-yl

OH

6: Nuc-leotides und Nuclric Acids

187

(%Iand (%)-diastereoisomers

of 9-(6-deoxy-a-L-talofuranosyl)adenine

cyclic

and (*)diastereo3',5-phosphoramidate (2312' and the closely related (9)isomers of 9-(6-deoxy-@-D-allofuranosyl)adenine cyclic 3',5'-phosphoramidate (24) have been reported.22 In both cases the compounds were ,prepared from the cyclic 3',5'-phosphate by activation with phosphoryl chloride followed ammonolysis.

by

The products were obtained in about 30% yield as a mixture of

diastereoisomers which could be separated by chromatography. Extensive n.m.r. studies have been performed to examine the conformation of the dioxaphosphorinane ring and these results have been used as evidence for the stereoelectronic control of their acid catalysed hydrolysis. propy1)guanine

and

Yoshikawa-type

phosphorylation

The cyclic phosphates of DHPG,

(g)-

9 - ( 3-hydroxymethyl-4-hydroxybutyl)guanine,

and

tested

(2)-9 - ( 2,3- dihydroxy-

and

(S)-9-(3,4-dihydroxybutyl)guanine

for

have been their

prepared

by

substratelinhibitor

properties on a wide variety of nucleases.23 2'.3'-Cyclic

phosphates of adenosine and guanosine are regioselectively

cleaved to 2'-phosphates at pH 11.0 using @ - and y-cyclodextrins as catalysts.24 In the case of adenosine 2',3'-cyclic phosphate the ratio of 2'-phosphate to 3'-phosphate was greater than 7:l.

Regioselectivity is ascribed to the forma-

tion of an inclusion complex in which the heterocycle is located in the cavity and results in very different environments for 0-2' and 0-3'.

Interestingly,

the regioselectivity is the reverse of that observed for a-cyclodextrin where

P-0-2' bond cleavage is almost exclusively favoured. A significant increase in both the selectivity and the rate constant for the P-cyclodextrin catalysed hydrolysis of adenosine 2',3'-cyclic phosphate was observed in the presence of sodium, potassium, rubidium and cesium ions.2 5

This catalytic enhancement is

probably due to coordination of alkali metal ions with the 0 - 3 ' atom facilitating P-0-3' bond cleavage. At pH 11.0 a-cyclodextrins have also been shown to induce regioselective cleavage of 3',5'-phosphodiester linkages in dinucleotides.26

Cleavage of CpA, CpC, CpG and CpU gave 96-97% of cytidine 3'-mono-

In the absence of phosphate together with A , C, G and U respectively. a-cyclodextrin hydrolysis (pH 11.0) of the same dinucleotides gives about 50X of cytidine 2' -monophosphate. (H,O)]z+

is

a very

The cobalt complex

[Co( triethylenetetramine)(OH)

efficient catalyst for the

hydrolysis of

adenosine

2',3'-cyclic phosphate to adenosine and gives a rate enhancement of about lo6 under mild conditions (pD 7.0, 20°C).27

This remarkable catalytic effect is

believed to result from both the attacking hydroxide ion and the 2',3'-cAMP coordinating to the same Co(II1)

species so that the reaction is effectively

intramolecular. 3 . Nucleoside Polyphosphates A very mild method has been described for the preparation of nucleoside

3',5'-bisphosphate~.~~Under tetrakistriazolide

reacts

strictly

with

anhydrous

nucleosides

to

conditions

form

pyrophosphoryl

a pyrophosphate

structure which bridges the 3 ' - and 5'-hydroxy functions.

ring

Hydrolysis of this

intermediate in the presence of triethylamine opens the pyrophosphate to form the 3',5'-bisphosphate. The procedure is particularly suited to the preparation of

acid

labile

nucleotides

and

has

been

applied

to

the

synthesis

of

bisphosphates derived from N_-2,3-etheno-2'-deoxyguanosine,e-2-ethyl-2'-deoxythymidine and ~-4-rnethyl-2'-deoxythymidine. Multigram quantities of CTP, GTP and UTP are available through a convenient enzymatic procedure."

Treatment of CMP with adenylate kinase, pyruvate kinase,

phosphoenolpyruvate and a catalytic amount of ATP gives CTP in 92% yield.

GTP

is prepared from GMP in 85% yield in a similar reaction, but with guanylate kinase replacing adenylate kinase.

In both procedures the relatively expensive

phosphoenolpyruvate can be generated in situ from the much cheaper D-3-phosphoglyceric acid.

Whilst UTP is also available from UMP through a purely enzymatic

synthesis it is most efficiently prepared (>95% yield) by deamination of CTP using sodium nitrite in acetic acid at 4°C. Bis(adenosin-5-yl) di-, tri- and tetraphosphates ( 2 5 ) have been synthesised by

metal

ion

catalysed

pyrophosphate

bond

formation

yield) were obtained with Mnz' and Cd"

between

adenosine

Best results (up to 60%

5' -phosphorimidazolide and adenosine nucleotides. 3 0

using a 3 fold excess of the imidazolide

over the nucleotide in 0.2 M N-ethylmorpholine-HC1 buffer at pH 7.0.

The exact

role of the metal is unclear, but most probably promotes pyrophosphate bond formation through coordination to the nucleotide andlor the imidazolide. The & of adenylated bis(nucleosid-5'-yl) tetraphosphates (Ap,N) has

vivo synthesis

been studied in strains of E.coli that overproduce aminoacyl-tRNA synthetases.31 Overproduction of any of the studied synthetases was accompanied by a significant increase in intracellular Ap,N

concentrations and the results establish

that aminoacyl-tRNA synthetases are

involved

in Ap,N

biosynthesis during

exponential cell growth and heat shock. Small nuclear RNAs (snRNAs) such as U1, U2, U4 and U5 possess a unique hypermethylated NZ,NZ-7-trimethylguanosine

cap structure

containing

(m3Z'2'7G) at their 5'-end. Several derivatives of

this cap structure have been

synthesised using

S-phenyl-Nz,N2-7-trimethyl-

guanosine 5'-phosphorothioate (26) as the key intermediate.32

Activation of

( 2 6 ) with iodine in the presence of the bis(tetrabuty1amnonium) salt of ADP or

GDP

gave

the

capped

nucleoside

triphosphates

M3'"'7G5'

ppp5'A

(27)

and

M32'2'7G5'pppS'G ( 2 8 ) respectively in about 50% yield. In an attempt

to

facilitate the uptake pyrophosphate

have

exploit of been

the mannose-6-phosphate receptor

nucleotides, nucleoside prepared.

adducts of

system to

D-mannose-6-

P1-(5-Iodo-2'-deoxyuridine)-5',P'-D-

6:

Nudeorides and Nuckeic Acids

189

mannose-6-pyrophosphate (29) was synthesised D-mannose-6-phosphate with

in 40% yield by

reaction of

S-iodo-2'-deoxyuridine 5'-phosphorom0rpholidate.~~

The adduct did not show any activity against strains of herpes simplex virus deficient in thymidine kinase and these results are indicative of pyrophosphate bond cleavage taking place prior to cellular uptake. 2',3'-Dideoxynucleoside S'-O_-(a-thio)triphosphates have been prepared by a one-pot synthesis from the precursor dideoxynucleosides and used in Sanger's dideoxynucleoside sequencing method.34

Sequencing reactions performed

with

these dideoxynucleoside analogues give chain termination products which are resistant to hydrolysis with exonuclease I11 and this enzyme can therefore be used to remove DNA fragments resulting from adventitious chain termination which

5'-0-

could otherwise interfere with the interpretation of the sequence data. Phosphorothioate analogues

of

5',5'-dinucleoside

oligophosphates

have

been

synthesised'fromthe 5'-G-phosphorothioate derivatives of 2',3'-2-isopropylidene adenosine.35 Activation of the phosphorothioate monoester with diphenylphosphorodichloridate followed by

reaction with the appropriate nucleoside

5'-2-mono-,di- or triphosphate and subsequent removal of the isopropylidene group with a strong acid ion exchange resin gives the required products in good yield.

Assignment of absolute configuration at the phosphorothioate centre was

performed on the pure diastereoisomers of the isopropylidene protected dinucleoside oligophosphates that had been separated by h.p.1.c. These products can be degraded to ADP(aS) by successive treatment with sodium periodate (pH 10.51,

a strong acid ion exchange resin and alkaline phosphatase and

the

configuration of the ADP(aS) can then be determined by the retention time on reverse-phase h.p.1.c. A

variety of interesting nucleoside imidophosphates have recently been

reported.

Reaction

of

N-methylimidodiphosphate

with

Sa-2-toluenesulphony1-

adenosine gives adenosine 5'-(a,P-N-methy1imido)diphosphate (30) which can be phosphorylated with phosphocreatine and 5 -(a, 0-N-methylimido)triphosphate (31).

creatine kinase to give adenosine

5' - (0, y -!-methylimido)

Adenosine

-

triphosphate (32) has also been prepared from adenosine 5'-monophosphate and N-methylimidodiphosphate 5'-(a.0-imido)diphosphate

to

that

described

for

by Michelson's p r o ~ e d u r e . ~ ~ 2'-Deoxythymidine (33) has been synthesised using a procedure analogous

(30)

and

was

shown

2' -deoxythymidine 5' -2-phosphoramidate over Adenosine S'-(a,P-irnido)diphosphate

a

to

undergo

period

of

decomposition several

to

days. 3 7

has also been prepared and its Properties

studied. s a

4.1

4. Oligo- and Polynucleotides Synthesis. Several review

DNA

articles on

protecting groups used in oligonucleotide synthesis"

DNA

synthesis

have appeared.

'*

and

In some

190

(29) 0 Me0

0 Me0 II

I

II

A&

HO-P-N-7-0 HO I HO

OH I HO

I

II

II

t

OH I

AH

0 Me0 II

I

OH I

bH

OH I

wA

OH

HO

OH

(31)

(30)

HO-P-N-P-0-P-0

II

HO-P-0-P-N-P-0

v!?

Ad0 HO-P-N-P-O I HO

Hb

yoy HO

HO

(33)

(32)

Hov 4

,c=o

\

N ,CH,CONHO

V B 0, ,OMe

I

R

7N(Pri),

(34)

(35) R = H (36)R = Me

CPG

6: Nucieotides and Nucdeic A c i A

191

cases reviews have concentrated on more specialised aspects of the area such as the use of ally1 protecting groups

41'42

and the synthesis of oligonucleotides

based on organometallic chemistty.43 The

development

of

new

nucleoside protecting groups

and

procedures continues to be an important part of DNA synthesis.

al.

have reported that in the presence of

protection

Bleasdale g

2,6-di-t-butyl-&-methylpyridine,

nucleosides are rapidly and very efficiently tritylated at the 5'-position using the tetrafluoroborate salts of either 4-methoxytrityl or 4,4'-dimetho~ytrityl.'+~ Standard solid-phase procedures for the synthesis of oligodeoxyribonucleotides necessitate repeated and in some cases prolonged exposure to acidic conditions for the deprotection of the 5'-hydroxy function.

The acidic conditions can

cause depurination of 2'-deoxyadenosine and for this reason DNA synthesis using nucleoside methoxyphosphoramidites containing the base labile S'-O-fluorenylmethoxycarbonyl (FMOC) group (34) has been examined.45

The 5'-FMOC group is

removed rapidly using a 10% solution of 1,8-diazabicyclo(5.5.O)undec-7-ene (DBU) in dichloromethane.

Unfortunately the use of DBU in conjunction with the

methoxyphosphoramidite necessitates two additional changes to the standard procedures. Firstly, the conventional linker (35) which is used to attach the 3'-terminal nucleotide to the controlled-pore glass support is unstable to the DBU treatment and about 1% of the oligonucleotide is cleaved from the support during each deprotection. The cleavage is believed to result from deprotonation of the nitrogen a i d e with DBU which cyclises by intramolecular nucleophilic attack on the ester carbonyl function; this adventitious oligonucleotide cleavage from the support is eliminated using the sarcosine derived linker ( 3 6 ) . Secondly, the N-3 position of 2'-deoxythymidine requires protection to avoid methylation at this position by reaction of the deprotonated nitrogen atom with the phosphite triester. The 2-(t-butyldiphenylsilyloxymethyl)benzoyl

(SiOHB) group (37) has been

used to protect the exocyclic amino groups of the 2'-deoxyribonucleosides of adenine, cytosine and guanine.4"

Treatment of the SiOMB protected nucleoside

with fluoride ion releases the benzylic hydroxy group which cyclises to liberate the nucleoside. The relatively fast and quantitative removal of this blocking group is attributed to a strong hydrogen bond formed in the transition state between the fluoride ion and the amino proton.

The utility of the SiOMB group

has been demonstrated by the preparation of a deoxyribonucleotide hexamer on solid-phase. Protection of the exocyclic amino groups of 2'-deoxyadenosine and 2'-deoxycytidine has also been accomplished with the 9-fluorenylmethoxycarbonyl group and this protection strategy in combination with phosphoramidite chemistry has been used for the synthesis of a 12-residue fragment of the human insulin @-chain gene.47 Surprisingly, it has been shown that in dry pyridine at 50°C,

a-phenyl cinnamoyl chloride reacts selectively with the exocyclic amino function of 2'-deoxyadenosine, 2'-deoxycytidine and

2'-deoxyguanosine with negligible

reaction with the sugar hydroxy functions.

Deprotection of the resulting

N-a-phenyl cinnamoyl nucleosides is readily achieved with the conventional treatment with concentrated aqueous amonia.

Additionally, the bulk and hydro-

phobicity of the phenyl cinnamoyl group confers resistance to acid catalysed depurination of 2'-deoxypurine nucleosides. been demonstrated

in the synthesis of

The application of this group has

a dodecanucleotide using both

the

phosphoramidite and phosphotriester approaches. A new strategy for the synthesis of oligodeoxyribonucleotides has been presented using a set of nucleoside 3'-(2-cyanoethyl)-~,~-diisopropylphosphoramidites in which the 4-nitrophenylethoxycarbonyl (NPEOC) group is used €or protection of the amino group."g The amide function of 2'-deoxyguanosine is additionally protected by the 4-nitrophenylethyl (NPE) group (e.g. 3 8 ) .

The NPE

and NPEOC groups as well as the cyanoethyl group are removed by treatment with

0.5 M DBU in acetonitrile for 6 hours.

Interestingly, when this strategy is

used in conjunction with a support containing a 1,6-bismethylaminohexane linker (391, all the protecting groups can be removed without cleaving the oligodeoxy-

ribonucleotide from the support.

Cleavage from the support is achieved with

concentrated aqueous m o n i a to give the crude oligodeoxyribonucleotide free of by-products.

A similar strategy has been employed by Noyori and co-workers

using allyl and allyloxycarbonyl groups to protect the internucleotide linkages and nucleoside bases respectively (e.g. 40).50 Synthesis was performed by the phosphoramidite approach on controlled-pore glass with a succinyl linker.

The

allyl protecting groups were efficiently removed by treatment with a mixture of tris( dibenzylideneacetone)dipalladium(O)

-

chloroform complex, triphenylphos-

phine, butylamine and formic acid at 50°C for 1 hour.

Once again cleavage of

the oligodeoxyribonucleotide from the support is accomplished with aqueous ammonia.

The efficiency of

this procedure has been

demonstrated in the

preparation of a 60-residue oligomer of unprecedented purity.

oligodeoxyribonucleotide synthesis on a soluble polymeric support combines aspects of traditional solution methods with solid-phase synthesis and

is

particularly suited to the preparation of intermediate quantities of small and medium sized oligorners. A high efficiency liquid-phase procedure has been developed using polyethylene glycol as the soluble support.5 1 5' -2-Dimethoxytrityl-2'-deoxynucleoside-3'-succinates can be attached to the polymer using

standard protocols and oligodeoxyribonucleotides of up to 8

residues were

synthesised by the phosphotriester approach using l-(2-mesitylenesulphonyl)-3nitro-l,2,4-triazole

(MSNT)

generally in excess of 9OX

and

N-methylimidazole.

Coupling

yields

were

and polymer bound oligodeoxyribonucleotide was

5:

Nuclrorides and Nuclcic Acids

DM 0

1

~ S i - - O C H 2 - C H - C H 2 0 C O N - ( C H 2 ) 16 - N - C O C H1 2 C H 2 C ~ I OAc CH3 CH3

(39)

0 H O - C H 2 - C H 2 - ~ ~ C H 2 - C H 2 d acetate - ~ ~ >

0

0

Organophosphorus Chemistry

194

separated from excess monomer and coupling agents by precipitation into ether followed by two crystallisations from ethanol.

Cellulose acetate fmctionalised

4-(2-hydroxyethylsulphonyl)dihydrocinnamoyl

with

similarly used

for

liquid-phase synthesis."

substituents

(41)

This

is

polymer

has

been

soluble

in

pyridine, but insoluble in ethanol and is therefore particularly well suited to the phosphotriester approach. exemplified

by

the

The effectiveness of this procedure has been

preparation

an

of

octadeoxyribonucleotide

and

an

undecadeoxyribonucleotide in quantities in excess of 10 mg. Whilst the phosphoramidite approach is, in general, the method of choice for

automated DNA

synthesis very

solution synthesis.

little has been reported on

its use for

Beiter and Pfleiderer have described the synthesis of all

16 of the fully protected di-2'-deoxyribonucleoside phosphotriesters and their thiophosphotriester analogues.53 the

The syntheses were performed by activation of 3'-[4-(nitrophenyl)ethyl]phos-

5'-O_-dimethoxytrityl-2'-deoxyribonucleoside

42) in the presence of the appropriate 3'-g-benzoyl-2'-

phoromorpholidites (e.g.

deoxyribonucleoside. Yields for the coupling reaction were generally about 60% prior

to

5'-~-Dimethoxytrityl-Z'-deoxyribonucleoside

oxidation.

diethylphosphoramidites

(e.g.

43)

have

been

prepared

by

3'-g-bis-

reaction

of

5' -2-dimethoxytrityl-2'-deoxyribonucleosides with tris(diethy1amino)phosphine the presence activated

of

with

tetrazole and

diisopropylamine."

5-(4-nitrophenyl)tetrazole

d(CCTAGCTAGG) on a solid-phase support.

and

The

have

coupling yields are

by

tetrazole

in excess of

been

used

to

in

can be prepare

The initial product of the reaction is

a dinucleoside phosphoramidite linkage (44) which corresponding Z-phosphonate

bisamidites

the

can be

converted to the

catalysed hydrolysis.

97% and once the

The average

synthesis is

complete

oxidation to the required phosphodiester linkages is achieved using an aqueous solution of

iodine.

amidite with

Alternatively, oxidation of

t-butylhydroperoxide can

be used

the dinucleoside phosphor-

to generate a phosphodiethyl-

amidate linkage.

Tris(1,1,1,3,3,3-hexafluoro-2-propyl)phosphite,

which

is

an

effective

reagent for the preparation of 2'-deoxyribonucleoside g-phosphonates,55'56 has been prepared by

an

improved procedure from PC1,

1,1,1,3,3,3-hexafluoro-Z-propoxide. 5 7

In

addition,

1,3-dimethyl-2-chloroimidazolinium chloride agent

for

oligonucleotide

Coupling efficiency was

synthesis

y&

(DMCI) the

and the lithium salt of it

is

has an

been

shown

efficient

that

coupling

H-phosphonate

indistinguishable from that achieved using pivaloyl

chloride, but DMCI has the advantage that it is a stable crystalline compound and has

good solubility in organic solvents.

preparation

of

A

simple procedure for the

2 ' -deoxyribonucleoside H-phosphonates

has

been

developed.

''

Reaction of phosphonic acid with a condensing agent (either pivaloyl chloride or

195

6: Nudeorides and Nucleic Acids

"

"

'

O

W

0 d (43)

(42)

DMTowB 3

l

r*

f

!

H

H

HO-Y-O-Y-OH

0.

P

-

O

v

(45)

B

DM &

o\ P-OMe

P--OCHZCHzCN

MeO'

2

(46)

Q

0 11-

BzO

(47)

S - C e O M e

OBz (48)

0-7-0OH

~ - S - - S - - ( C H ~ ) ~ ~ - - N 0 (49)

d(AAAACGACGGCCAGTC)

5,5-dimethyl-2-oxo-2-chloro-l,3,2-dioxaphosphorinane) gives the pyrophosphonate

(45) which reacts smoothly with a suitably protected nucleoside to give the desired 3'-!-phosphonate

in yields greater than 85%.

The mechanism of inter-

nucleotide bond formation and the nature of unwanted side reactions for the H-phosphonate approach have been studied in detail."

Side reactions that occur

on activation can be minimised by using acetonitrile-quinoline ( 4 : l ) as solvent. This improvement to the procedure has been exemplified in the synthesis o f

n

38-residue deoxyribonucleotide. has

Surprisingly, it

been

shown

that

upon

activation

with

iodine,

phosphites (e.g. 46) can b e used f o r

bis(deoxyribonucleosid-3'-yl)-2-cyanoethyl

the synthesis of dinucleoside phosphates on a solid-phase support.Ga These results led

the authors to investigate the .utility of deoxyribonucleoside

3'-dimethylphosphites (e.g. 47) for oligonucleotide synthesis. However, whilst (47) could be activated with iodine and reacted with a 5'-hydroxy group of an otherwise protected nucleoside to give the fully protected dinucleoside methyl phosphitetriester in good yield, the accumulation of side reactions produced poor yields of oligonucleotides on solid-phase synthesis.

The

solid-phase

synthesis of oligodeoxyribonucleotides by iodine activation of (47) has also been investigated by Potapov, and the overall yield for the synthesis of dT,, was 11%after deprotection and isolation.61 An ingenious procedure for the combined purification and phosphorylation of oligodeoxyribonucleotides has been developed that relies upon the use of a 2',3'-~-dibenzoyl-3-undecyluridine 5'-(2-cyanoethyl)-kJ,l-diisopropylphosphorami-

dite (48).62 This residue is introduced in the final coupling step and after deprotection the thiol function can be released by treatment with silver nitrate followed by dithiothreitol

The thiol containing oligonucleotide can then be

coupled to controlled-pore glass also bearing thiol functions through a disulphide bridge ( 4 9 ) .

After separation of the support and washing, the required se-

quence is liberated with sodium periodate and triethylamine to give the 5'-phosphorylated oligonucleotide.

Bis(allyloxy)(diisopropylamino)phosphine

(SO) can

also be employed for the 5'-phosphorylation of nucleosides and oligodeoxyribonucleotides.b3 Activation with tetrazole in the usual manner and reaction with a nucleosidic 5'-hydroxy group followed by oxidation with m-chloroperbenzoic acid gives a fully

protected 5'-phosphate in excellent yield.

The ally1

protecting groups are removed with tetrakis( triphenylphosphine) palladiwn(0). Reverse-phase h.p.1.c. purification of

very

has

long

oligodeoxyribonucleotides."

been

(88-143

The

demonstrated to be bases)

isolated

effective for the

5'-~-dimethoxytrityl-derivatised

yields

were

superior

to

those

obtained using electrophoresis followed by electroelution. A fast procedure has been reported for the

purification of

oligodeoxyribonucleotides of varying

197

6: Nucleotidrs and Nucleic Acids

Cl (51 )

5‘ HO-protected

oligodeoxyribonucleotide

I

duplex

5’ 5’ 3’

1

T T T T T

I

A-T A-T A-T A-T A-T

I

O

F

T

? O=P-OH

h

Y

15

- linker

T-A T-A T-A

T T T

T-A

T

?

O=P-OH

c--Gc

bTh

0 I

Organophosphorus ChrmistT

198

lengths (10-40 bases) by anion exchange h.p.1.c. using volatile buffers.65 Several interesting strategies have appeared for the synthesis of cyclic oligodeoxyr-ibonucleotides.

A versatile solid-phase procedure has been developed

in which fully protected nucleoside phosphate triesters were attached to a polyacrylamide support & y

the heterocyclic bases (exocyclic amino groups of dA

dC or dG and N-3 or 0-4 of T e.g. 51)." the

5'-position, after

Chain extension can occur from either

treatment with

3'-terminus following removal of

trichloroacetic acid,

the cyanoethyl

or

group with

from

the

triethylamine.

Cyclisation is performed by deprotection of both 5'- and 3'-ends followed by treatment with (MSNT) and subsequent cleavage from the polyacrylamide resin is achieved

by

standard

aamonolysis.

hexadeoxyribonucleoiides

Cyclic

have been prepared

phosphotriester approach."

di-,

tri-,

in solution

tetra-, by

penta-

the

and

filtration

A key part of the strategy involves the use of

nucleoside 3'-(2-chlorophenyl) (2,4-dinitrobenzyl) phosphates as a 3'-terminal building block (e.g.

52).

Once the oligodeoxyribonucleotide has reached the

desired length the dinitrobenzyl (DNB) group is removed by a brief treatment with toluene-4-thiolate ions and the resulting 3'-tenninal phosphate diester cyclised to the 5'-hydroxy group with MSNT in anhydrous pyridine.

The yield for

the combined steps of DNB removal and cyclisation were generally greater than A less rigorous approach to cyclic oligodeoxyribonucleotides has been

60%.

adopted cyclised

by

g &. "

3' ,5 ' -Unprotected

bifunctional

phosphorylating

Capobianco using

a

linear precursors reagent

were

2-chlorophenyl

bis-~,~-(l-benzotriazolyl)phosphate. The procedure is particularly amenable to the synthesis of millimolar quantities of relatively short cyclic oligonucleotides.

A topologically more complex DNA structure in the form of a specific

quadrilateral has

been prepared. "

Four different

three-am

branched

DNA

junctions, each composed of two oligodeoxyribonucleotides were synthesised and covalently linked

together by

enzymatic ligation.

The product

is a

DNA

quadrilateral with sides of 16 base pairs long (approximately 1.5 turns of the helix).

Each individual junction is closed by a hair-pin loop and topologically

the four junctions form two intersecting DNA circles which are linked 6 times. A bidirectional pyrimidine oligodeoxyribonucleotide which contains a 3'-3' phosphodiester linkage with an abasic nucleoside (as in 53) has been synthesised by

an

automated

2'-deoxynucleoside.

procedure

starting

from

a

5'-O_-support

bound

The oligodeoxyribonucleotide is able to bind to adjacent

purine tracts on alternate strands of a Watson-Crick duplex through triple-helix formation. The abasic nucleoside acts as a linker between the adjacent strands. This work extends triple-helix formation to the recognition of (purinelm NN (pyrimidine)n sequences. Triple-helix formation has also been used to develop a chemical method for the ligation of two pyrimidine oligodeoxyribonucleotides.

6: Nucleoiides and Nucleic Acids

199

The double-stranded DNA serves as a template to align the reactive termini of the pyrimidine oligonucleotides (54).7'

The pyrimidine sequences are complemen-

tary in a Hoogsteen sense to the purine strand and the 3'-hydroxy function of oligonucleotide A is thus proximal to the 5'-phosphate of oligonucleotide B. Ligation is brought about by activation of the phosphate with cyanogen bromide in the presence of imidazole and NiC1,.

A pyrophosphate linked analogue of polycytidylic acid has been prepared from Ij-4-diphenylacetyl-2'-deoxycytidine phosphorothioate (SS).72

3'-O_-phosphate S'-O_-(S-4-methylphenyl)

Activation of (55) with iodine in a non-nucleophilic

solvent followed by removal of the diphenylacetyl groups with aqueous ammonia gave the 3',5'-pyrophosphate linked oligomers (56) and the cyclicpyrophosphate (57).

After fractionation, oligomers with a chain length greater than 16

residues (average length approximately 20) were used to catalyse the template directed

oligomerisation

of

3',5'-bisphosphoimidazolide

4.2

RNA Synthesis.

the

complementary

monomer

2'-deoxyguanosine

(58).

The chemical synthesis of RNA and its application to

molecular biology has been reviewed.73 The choice of a permanent protecting group for the 2'-hydroxy function is of paramount importance in oligoribonucleotide synthesis.

The 2-nitrobenzyl

group has been effectively used for the protection of this position and can be quantitatively removed by photolysis after chain construction.7 4

However, in

some instances deprotection is less than quantitative and yields are not improved by further irradiation. Model studies have shown that in the presence of

oxygen,

photolysis

Z'-O-(Z-nitrobenzoyl) conditions.75 the

with

long

derivatives

W

wave

which

are

light

can

stable

to

give the

rise

to

irradiation

These oxidative side reactions can be eliminated by performing

photolysis

at pH

l-(2-chloroethoxy)ethyl

3.5

in

solutions

purged

with

nitrogen.

The

(CEE) group has been used as an acid labile blocking

group for the 2'-hydroxy function and is presented as an alternative to the tetrahydropyranyl (THP) group.76

It is more resistant to acid cleavage than THP

ethers and therefore allows repeated removal of a DMT group without concomitant deprotection of the 2'-position,

The CEE group has been used in combination

with

(e.g.

phosphoramidite

chemistry

59)

for

the

preparation

of

a

integrity

of

dodecaribonucleotide on solid-phase. A

detailed

n.m.r.

oligoribonucleotides

study

prepared

has

been

by

the

procedure with Z'-O-t-butyldimethylsilyl

undertaken automated

on

the

cyanoethylphosphoramidite

The n.m.r. studies in

conjunction with enzymatic digestion (ribonuclease T,) demonstrate that the oligoribonucleotides contain entirely 3',5'-phosphate linkages and chemically

Organophosphorns Chemisrty

200

duplex 3' 5' C-GC T-A T T-A T T-A T C-GC

T-A T T-A T T-A T T-A T G - G C T-A T C - G C

I I

A

B (55)

I (54)

I

440 /p\

"O

OHO,? Y

C

9

PI

IU-\

HO

/O

6: Nucleotides and Nucleic Acids

20 1

prepared AGCU was essentially indistinguishable from the same sequence prepared using

polynucleotide

phosphorylase.

and/or 3'-5'

containing 2'-5'

Sequence

defined

oligoribonucleotides

phosphodiester linkages have

been

using 5'-protected ribonucleoside 2',3'-cyclicphosphoramidites

synthesised

(e.g 60).'8

activation with 5-(4-nitrophenyl)tetrazole (60) can be coupled to a support bound ribonucleoside and on oxidation (aqueous iodine) a mixture of the 2l-5' and 3'-5'

linked dinucleotides are formed (61).

of 2'-5' and 3'-5'

After deprotection, the ratio

linkage isomers could be quantified by h.p.1.c.

and the ratio

was found to be dependent on the heterocyclic bases present. The

1,1,1,3,3,3-hexafluoro-2-propyl

(HFP)

group has been

used

phosphate protecting group for oligoribonucleotide synthesis.'g phosphoryl chloride with 1,1,1,3,3,3-hexafluoro-2-propanol

as a new

Reaction of

in the presence of

aluminium chloride gives the hexafluoro-2-propyl phosphorodichloridate Phasphorylation nucleosides with

(62).

~-acyl-5'-~-dimethoxytrityl-2'-~-tetrahydropyranyl

of

(62) in the presence of triazole and subsequent hydrolysis

yields the phosphodiester monomer

Short segments of RNA have

(63).

been

prepared from (63) by the phosphotriester approach using 8-quinolinesulphonyl chloride and N-methylimidazole as coupling agents.

Removal of the HFP group is

achieved with a standard o x b a t e treatment. An improvement has been reported to the synthesis of oligoribonucleotides by the 1-hydroxybenzotriazole-activated The activated intermediates (e.g. 64) are extremely

phosphotriester approach.

sensitive to moisture and readily hydrolysed.

Additionally, the hydroxybenzo-

triazole generated on hydrolysis can cause partial removal of the DNT group. The addition of dicyelohexylcarbodiimide

stabilises the intermediates towards

hydrolysis and does not cause untoward side reactions.

This modified procedure

has been applied to the synthesis of two oligoribonucleotides r(GCGAAAGC) and r(CGAAAGC). 297

24 RNA Fragments corresponding to the hop stunt viroid (total of

residues)

approach.'l

have

been

synthesised

by

9-Phenylxanthen-9-yl (pixyl) and

(Hoxyl) groups

were

used

nucleosides respectively.

for The

5'-protection

the

cyanoethyl

phosphoramidite

9-(4-methoxyl)phenylxanthen-9-y1 of

the

purine

tetrahydropyranyl group was

and

pyrimidine

utilised

in

the

blocking of the 2'-hydroxy function and the bases were protected as shown in (65).

Average coupling yields were in the order of 95% using a solid-phase

procedure on CPG.

A series of oligoribonucleotides (6-29 residues) have been

prepared in yields up to 44% using N-acyl-5' -_O-dimethoxytrityl-2' -g-tetrahydropyranyl 3'-!-phosphonates mixed

DNA-RNA

activated with pivaloyl chloride.82

oligomers has

deoxyribonucleoside

been achieved

phosphoramidite

phosphoramidite intermediates."

and

on a

Synthesis of

solid-phase support

2'-silylated

using

ribonucleoside

Deprotection was accomplished using standard

procedures for oligoribonucleotides and the mixed oligomers have been used to

302

DMTov (59)

DMTowB 0,o

DM DMTo O\\dO OTHP HO” ‘OCH(CF&

I P -N(PTi)2 R / NCCH2CH20 (65)

B = N 6-benzoyladenin-9-yl; R = H B = N*-propionyl-O 6diphenylcarbamoylguanin-9-yl; R = H B = N 3-anisoyluracil-l -yl; R = OMe B = N4-anisoylcytosin-1-yl; R = OMe

6: Nucleotides and Nucleic Acids study

RNA

catalysis.

203 Strategies

oligoribonucleotides formed

in the

for

the

synthesis

of

branched

pre-mRNA splicing reactions have

been

c~mpared.~' Phosphite triesterk and phosphate diesters are relatively stable to attack by a vicinal hydroxy group under neutral and mild acid conditions and therefore synthetic methods attractive.

involving these intermediates are particularly

A strategy based on the use of ally1 protecting groups has also

been used in the regiocontrolled synthesis of branched oligoribonusleotides.85 In a monumental work Reese and co-workers have reported the synthesis of the 37-residue 3'-terminal half

( 6 6 ) of

phosphotriester approach in solution.'6'87

alanine tRNA from yeast using the The protecting group strategy for a

solution synthesis of this complexity is particularly important and previous work on the synthesis of a 3'-terminal nonadecaribonucleoside had established the need for protection of 0-6 on guanine and 0-4 on uracil.'' earlier

studies,

guanine

bases

were

Based on these

protected

as

the

6-0_-(3-chlorophenyl)-2-~-phenylacetyl derivatives (67); 0-4 on uracil bases was

blocked by the 2.4-dimethylphenyl group (68) and the amino functions on adenine and cytosine bases were simply protected as the 4-(t-butyl)benzoyl

(69) and (70) respectively.a6 The modified base pseudouridine

(Y)

derivatives

was protected

at the N-1-position with the 4-bromobenzenesulphonyl group whilst 5-methyluracil

(T) was protected

as

the g-4-phenyl derivative.

The methoxytetrahydropyranyl

group was used for the permanent protection of the 2'-hydroxy functions. in'tial

strategy was to use the 2-(dibromomethy1)benzoyl

The

(Dbmb) group for the

temporary blocking of the 5'-hydroxy function.

However, removal of this group

using silver perchlorate in collidine became

increasingly inefficient with

increasing chain length and the Dbmb group was successfully replaced with the 2-(isopropylthiomethoxymethyl)benzoyl (Ptmt) group (71) which was rapidly removed

with mercury I1 perchlorate under similar conditions. The oligoribonucleotides were

assembled

in

solution

by

the

phosphotriester

approach

using

the

2-chlorophenyl group to protect the internucleotide linkages and MSNT. as the condensing agent. three

step

The final 37-residue oligoribonucleotide was deprotected in a

procedure

using

sequentially

E-2-nitrobenzaldehyde

concentrated aqueous annnonia and 0.01 M hydrochloric acid.

oximate,

The total synthesis

of yeast tRNAAla by a combination of chemical and enzymatic methods has also been completed." A 35-residue oligoribonucleotide constituting the 5'-end of the initiator tRNA from B.subtilis has been synthesised on solid-phase using phosphoramidite chemistry in combination with 2'-0_-t-butyldimethylsilyl protection."

For the

protection of the exocyclic amino functions of the bases the phenoxyacetyl group was used for adenine and guanine whilst acetyl was preferred for cytosine. These comparatively acid labile acyl groups can be removed using relatively mild

204

Organophosphorus Chemistry

3' A C C A C C C G C U C AGGCC u UCCGG T C U G

G A G A G G

a

0

u

A

w

C

G

CI

6: Nurleotides and Nurleic Acids

205

conditions in the annnonia deprotection step and enable 5,6-dihydrouridine, which is present in the sequence and is sensitive to alkaline conditions, to be successfully incorporated into the oligoribonucleotide. The synthesis of aminoacyl oligoribonucleotides that mimic the role of the tRNA 3'-terminus has attracted considerable attention and recently Hagan and '

Chladek have synthesised ~henylalanine.~' The

' GGA3

I

aminoacylated at

oligoribonucleotide

was

the 2'(3')-position

assembled

by

the

with

stepwise

phosphotriester approach using (72) as the building block for the incorporation of

guanosine.

Aminoacylation

of

the

2- ( 4 4 ' -biphenyl)- 2- ( propyloxycarbony1)

trinucleotide protected

presence of l-(2-mesitylenesulphonyl)tetrazole. the 2'(3')-g-(L-phenylalanine)

was

performed

L- phenylalanine

using

in

the

Complete deprotection to give

trinucleotide was accomplished

by a

standard

oximate treatment followed by a removal of acid labile groups in 80% form.. acid at 0°C for 30 minutes.

A

hybrid

dinucleotide

pdCpA

has

L-phenylalanine to give pdCpA-Phe.92

been

chemically

aminoacylated

with

The aminoacylated dinucleotide can be

used in an enzymatic ligation (T4 RNA ligase) and attached to the 3'-terminus of a truncated (3'-terminal CA residues missing) amber suppressor tRNACUA. resultant

chemically

aminoacylated

tRNA

can

be

used

L-phenylalanine in response to an amber nonsense coding.

The

incorporate

to

This procedure can

potentially be used for the site specific incorporation of an unnatural amino acid

into proteins.

The use of deoxycytidine at position 75

in the tRNA

greatly simplifies the synthetic chemistry and does not appear to affect the efficiency of the tRNA. E.coli

tRNAfMet

in

Ogilvie and co-workers have prepared a DNA analogue of which

all

the

uridine

residues

are

replaced

by

2'-deoxythymidine and all residues are deoxyribonucleosides with the exception of the 3'-terminal riboadenosine."

This tRNA analogue can be aminoacylated by

E.coli methionyl-tRNA synthetase and the results support the hypothesis that aminoacylation of tRNAfMet does not depend on the presence of 2'-hydroxy groups with the exception of that in the 3'-terminal nucleotide. Catalytic activity of ribonucleic acid has been reviewed"

together with

its implications for the origins of life." 4.3

Oliaonucleotides Containing Modified Phosphodiester Linkages.

synthesis of

oligo- and

polynucleotides

containing modified

Whilst the

phosphodiester

linkages dates back to the 1960'~,'~ the knowledge that these analogues can both inhibit

and

interest in

activate this

gene

area, and

anti-sense oligonucleotides.

expression given

has

rise

to

dramatically a

new

increased

therapeutic

research principle;

The s y n t h e s i ~ ~ and ~ ,propertiesg7 ~~ of anti-sense

oligonucleotides have recently been reviewed.

Orgunophasphomv l. High polyiodide concentrations give high conductivity by a process involving iodide transfer between polyanions 259-260 Radiation

.

crosslinking of MEEP-LiCF,SO, does not lower the conductivity. 261 Mixed polymer electrolytes consisting of Li+ salts of MEEP and poly(ethy1ene oxide) have higher conductivities than those involving only poly(ethy1ene oxide) salts.

Systems containing mixed LiBF,, and LiC10, salts give the best conductivity. 262 Sodium ion complexes of phosphazenes with covalently bound sulfonates have been examined.253 Aminophosphazene polymers such as [NP(NHPh),In become electrically conductive when treated with C1S0,H.264 The use of poly(ph0sphazenes) as membranes for separations has recently attracted interest. The gas transport parameters for 14 gases across PTFE films have been measured with a high selectivity towards CO, being noted.265 The oxygen gas permeability of 15 different poly(phosphazenes), including phenoxide, alkoxide and amino derivatives, in water has been measured with [ NP (NEt,) (NHCMe,) 3 having the highest value. 256 The 0, permeability and O,/N, selectivity of multilayer membranes consisting of porous substrates which enclose a poly (phosphazene) middle layer have been measured. 267 Diffusion of solutions of Cr3+, Co2+ and Mn2+ ions through a PTFE membrane allows for separation of Cr3+ from the remaining ions.268 Thermal stability of polymeric materials is a significant consideration in many poly(ph0sphazene) applications. The kinetics of the thermal degradation of PTFE are best fit with a model requiring a two step initiation for depolymerization. These steps involve formation of defect units, such as =P(O)NH- and =P(0)N(CH2CF3)-, which become active centers for d e p o l y m e r i ~ a t i o n . ~Mixed ~~ fluoroalkoxyphosphazene rubber materials are more resistant to abrasion and tearing than fluorosilicone but have poor long term properties in air at elevated temperature^.^^' The isothermal weight loss has been used to evaluate the thermal A stability of an elastomeric poly (phosphazene)

.,”

comparative study of fireproofing effectiveness in epoxy resins of cyclic, linear polymeric and cyclolinear polymeric phosphazenes with alkoxy, phenoxy and fluoroalkoxy substituents has been examined with linear fluoroalkoxy species being found to be most effective.2n Patents describing specific applications or formulations are available. Specific items which appeared include: aryloxyphosphazenes for flame-retardant panels2n and fibers MEEP-LiCF,SO, based thermally actuated secondary hydrogen

, 274

8: Phospha w n es

327

battery275, PTFE films for insulation of printed circuits226and lift-off mask for A1 film patterns2n, [NP(OPh),], resist layers,2T8additives for epoxy resins used for potting semiconductors,279 MEEP-KCF3S03 to effect antistatic properties in photographic film2B0,crosslinked mouldings based on fluoroalkoxyphosphazenes, rigid poly (phosphazene) foams282, bioerodible phosphazenes for sustained-release of pharmaceuticals2= and activated fluoroalkoxyphosphazenes as carriers for enzyme immobilization.m 7.

Holooular Structures of Phoppharones.

The following structures have been determined, except where noted, by x-ray diffraction. All distances are in picometers and angles in degrees.

ComBound PhN=PCl (NEt,),*AlCl,

Comments PN bonds equal, mean 160 one N pyramidal, others planar

(morph),PNl=N N+, (Et) c6H2 (NO,) morph=morpho fino

PN, 168.4(1) : N,+ 127.2(2) N2N3, 131.2(2) PN, 165.1(1) N,N,127. 9 (1) LPNlN2 109.5 (1) H-bonding to N,.

2

No data given

CH, ( PPh2=NC6H,-p-Me)

PN 156.8(2), 156.6(2)

CH, ( PMe,=NC,H,-p-NO,)

,

[ Mo ( NFWe,) C1, ( PMe,) 3]C1

[ ( P M 8 3 ) 2C1,MoN140C13( PMe,) ,] [ Me,PNPMe,

N,P3C1,NHC (0) OEt

I

Ree. 8

13

13,14

32 20

PN 158.0(4)

20

PN 163.6(4) LMoNP 167.6 (3)

22

PN156.4(6), 156.0(6) LPNP 141.7(5)

22

Chair PNd 160.2 PNcxo164.1-166.0 LPNP 122O, LNPN 115 H-bonding gives dimers of cofacial rings.

92

slightly pucked mean PN 157.0(5) PNexo166.2 (6) LNPN 117.6 (6)i LPNP 121.4 (3) H-bridged dimer

285

Ref.

Comments twist boat P3N3 mean PN,,, 166 PN&,

99

160.1(4), 161.8(7)

P3N3 planar 286 , N P at sub. P 158-162 others 155.1 (6)-157.1 (6) PN,,, 162.4 (5) , 162.3 (6) 287 P3N3 Planar , N P 153.1 (13)-163.5 (11) PN,,, 160.4 ( 11) 165.6 ( 12 )

-

P3N3 Non-planar

, N P PN,,, 36

37

287

156.1 (9)=160.9 159.6 (9)-161.2 (9)

P3N3 non-planar 288 , N P 156.0(8)-160.5(8) ; 160.1(7)-160.9 (7) PN,,, 162.7(8), 162.6(7) 160.7(5) P3N3 planar 288 153.4 (10)-162.3 (8) PN,,, 166 (2), 162 (2)

,N P 9

allotrope of structure in ref. 286 differ in spiro loop conf.; P3N3 planar

104

, N P 158-162; 155.7-158.9 LPNP (endo) 112.7 at sub. P; PN,,, 160-164 , N P 154.2 (9)-163 (1) PNqxo163 (1)-167 (1)

106

spiro rings highly unsymmetrical , N P 155.815)162.5 (6) PNvo 16 3.7 ( 4 ) 165.0 ( 6)

106

-

spiro rings unsymmetrical trans 2,4 sub. on P,N, Macrocycle chair ,N P PN,,, 2,2’ -N3P3C1,(Ph)PPh2

289

156.0 (5)-159.5 (4) 161.1(5), 161.5(4)

angles at sub. P: LCPP=106.7 (1),

109

LNPN 114.5(2) PN=161.1(5), 161.9(5) at

sub. P, 151.1(3), 156.1(3),

157.0

8: Phospharettts

3 29 PP=2 19.9 ( 2 )

ComDound

Comments

,

2,2' -N,P,Cl, (Ph)[ PPh,. Cr (CO) ]

angles at sub. PLCPPE107.0(2), LNPN=114.8 PN=160.7 (5), 160.2 (2) at sub. P, 155.3(0)158.7 (7) Pw223.4 (2)

2,2 -N3P,C1, (Ph)[ PPh,*Ru, (CO)11 3

Two forms diff. with

Ref. 109

109 orient. of PPh,; angles at sub. P LCPP 102.3(7), 104.3(7), LNPN 116.7(9), 115.1(8) PN 157-162; 157-159; 153-157 N3P3 slight crown conf. PN 160-6 (5), 154.0 (5) 158 (1)

290

highly distorted boat 171 PN 157.7(3), 159.7(3), 163.3(4), 168.8(3) ; LNPN 108.5(2), 113.6(2) ( 18 CH,) *CF,SO,-

E=S

Methyl on N; PN 159.1(6), 166.6(5); 163.0(5), 162.8 (6)

172

17 E=Se, X=C1, Y=Ph

Se out of P,N, plane; 291 PN 163.7(5), 158.4(4) LNPN 117.8(2)

19 R1=Ph, R=Me, E=Se

chair, Se above N, plane; PN 162.3(3), 159.2 (3)

39 (R=tolyl)

rings nearly parallel, LNSS=102.5, 96.7; PN 160.4 (6)-163.3 (6) S-S 248.9(9)

40

3 coord. N down from 174 plane, 3 coord. Se up from plane of its ring, LSeNSe 118.7 (8) PN 156.5( 15)-165.4 (14)

41 ( R=C,H,,N)

P=N 159.5(3) ; PNC,H,, 161.9 (3)-163.9 (3)

25

PN,,, 159.9 (5), , N P 161.1(5), 162.4(5) exo LPNS 118.7(3)

173

174

177 175

330

Organophosphorus Chemis[?

t

8: Phosp ha m w s

33 1 Comments

COrnDOUM [NPMe (NSOPh ) 2]

C6H,

24 E=P, X=F

25

Ref.

P-P 221.6(9);

one enantioneric form; Me trans; PN 161.4(2)

178

Electron diffraction PN 157.9(10) LNPN 109-2 (7)

180

ring nearly planar: 181 , , N P 163.0(3) I 163.4(3) PN,,, 169.3 (3)

19 E=C, R=Ph, R,'=Ph,

C1

trans Ph(C1) configuration mean PN 156.9 boat like; 2 coord. P

42 CH,Cl,

182

183

out of N plane PN 159.9(1) I 159.2(1) LPPN 120.78(4) , 120.29(4) 42 PdC1,

PdC1, forms transannular 183 bridge between 2 coord. P; PN 160.2(7) , 160.3(7) LPPN 120.1

27 M=In, X=Y=2

DMF bound to each In: PN 157.0(3)

184

27 M=Sn, X=3, Y=l

PN=161.1(11) I 161.0 (11)

184

27 M=Fe X=Y=2

PN=160.6 (5), 160.9 (5)

184

24 E=V, X=C1, n=2

nearly planar 18 5 PN 159.3(3) I 161.2(4) LVNP 129.0(3) LPNP 121.3 (4)

28 X=C1

186 MeCN adduct at Ti PN 162.2(2) , 161.6(3) LNPN 98.0(1)

,

28 X=NPPh,N ( SiMe3)

186 , N P 160.4(9) I 161.3 (8): P=NCXO156.1 (9) PN (SiMe,) 164.9 (3) LNPN,, 101.6(4)

29

PN 160.4(4), 161.7(3) LNPN 101.6 (2)

186

PN=160-8 [3)

187

31 R=tolyl ; R' =PPh,NH (tolyl) $=COD

PN,,, , N P

188

32

distorted OH at Mo PN 165.3(6) I 162.1(6)

Cl$bONbCl,N=PPh,

( CH),PPh,=h

165.8 (10) 161.3(8)

189

332 ComDountJ

!3m!wJb

33 n=1, Q=P, M=Pd, L=C12

ESiMe, replaced by H

PN 159.9(6) LPNPd 115.4(3)

17 Y-Ph, E=Se, X=C1

PN 161.3(2),

(43)C1-

PN=160.3(11), 162.0(9)

1.

2. 3. 4. 5.

6. 7. 8.

9. 10.

11. 12. 13.

15. 16. 17. 18. 19. 20. 21. 22. 23.

164.2(2)

21 25 25

M.Witt and H.W. Roesky, polvhedron, 1989, 8, 1793. K.F. Ferris and C.B. Duke, Jnt J. Quantum. Chem.. Quantum Chem. S m . , 1989, a,397. T.M. Nguyen and T.K. Ha, Chem. Phvs. Lett, , 1989, 158, 135. W.W. Schoeller and T. Busch, Chem. Ber., 1990, 123, 971. A.N. Chernega, A.A. Korkin, M.Yu Antipin, Yu. T. Struckov, A.V. Ruban and V.D. Romanenko, J. Gen. Chem. USSR (Enal. Trans.), 1989, 59, 2001. E.N. Tsvekov and A.A. Korkin, J. Gen. Chem. USSR fEnsl. Transl.). 1989, 849. R. Ahlirichs, M. Bar, H.S. Pitt and H. Schnochel, Chem. pbvs. Jletterg, 1989, 1791. M.R. Mazieres, T.C. Kim, R. Wolf, M. Sanchez and J. Jand, g, Kristalloar. 1988, 147. A. Widelov and B. Folkesson and C. Andersson, SDectroscow L e t t . , 1989, 1101. W.N. Chou, M. Pomerahtz and M.K. Witzcak, J. Ors. Chem., 1990, 55, 716. G.D’Halluin, R. DeJaeger and P. Potin, pull SOC. Chim. Bels., 1989, 98, 653. R. I. Yurchenko, T.I. Klepa, E.E. Lavrova, V.P. Tikhonov and A.G. Yurchenko, J. Gen. Chem. USSR (Ensl, Trans.1 1 1989, B, 1796. V.P. Kukhar, L.F. Kasukhin, M.P. Ponomarchuk, A.N. Chernega, M.Yu. Antipin and Yu. T. Struckkov, phosr,horus Sulfur. Silicon, 1989, 44, 149. A.N. Chernega, M.Yu. Antipin, Yu. T. Struchkov, M.P. Ponomarchuk, L.F. Kasukhin and V.P. Kukhar, J. Gen. Chem. USSR. (Ensl. Trans-), 1989, 2 , 1113. W. Wolfsberger, Chem.-Ztq , 1989, 351 (Chem. Ab st. 1990, u,235437t). N. A. Tikhonina, A.A. Khodah and V.A. Gilyarov, Izv. d. Nauk SSR. Sec. 1990, 465 ( B t , 1990, J J J , 198580m). W. Wolfsberger, Ghem.-Zta 1989, 113, 156 Ab st., 1990, u,118943~). W. Wolfsberger, Q p n .-Ztq, 1988, U , 379 (Chem. Abst., 1990, u,359865). R.S. Edmundson, I. Forth and T.J. King, J. Chem. Res,, Svnog. 1989, 122. P. Imhoff, R. van Asselt, C.J. Elsevier, K. Vrieze, K. Guybitg, K.F. van Malssen and C.H. Stam, -p Sulfur. Silicon, 1990, 42, 401. K.V. Katti, R.G. Cavell, R.J. Batchelor and F.W. B. Einstein, m r a . Chem 1990, 2,808. V.C. Gibson, D.N. Williams and W. Clegg, J. Chem. SOC. w m . C o y n m , 1989, 1863. H.F. Sleiman, S. Mercer and L. McElwee-White, J. Am. chem, SOC., 1989, JJl,8007.

.

s,

m, m, a,

.

a

14.

BsL

.

.

u,

m.,

.

.,

(m.

8: Phosphuzenes 24. 25. 26. 27. 28.

333

R.W. Saalfrank, E. Ackermann, M. Fisher, U. Wirth, H. Zimmermann, -em. Ber., 1990, ;Lzz, 115. H.W. Roesky, U. Schloz and M. Noltemeyer, 8 . Anoru. Alls. Chem., 1989, 255. M. Pomerantz, S.K. Xi and S. Bittner, PhOSDhOrus Sulfur , 1988, X I 13. L.N Markovskii, D.M. Rudkevich and V.I. Kal'chenko, JEen. Chem. USSB m a l . Transl.), 1989, %, 2143. M. Yu. Dmitrichenko, V.I. Donskikh, V.G. Rozinov, G.V. Dolgushin, V.G. Ratovskii, V.G. Efremov and V.V. Rybkina, J. Gen. Chem. USSR fmul. T r W . 1 . 1989, 196. R.D. Gareev, E.S. Batyeva, I.M. Shermergonn, V.A. Al'fonsov and A.N. Pukovik, g-va. fz-, 1989, 256 (Chem.,1989, u, 214700n). A.V. Ruban, L.S. Kachkovskaya, M.I. Povolotskii, V.D. Romanenko and L.N. Markovskii, J, Gen. Chem. USSR [En& -1.1 1989, B,1910. L.N. Markovskii, Yu. G. Shermolovich, V.Yu. Abramov, V.S. Talanov and V.I. Staninets, J. Gen. Chem. USSR (En& Transl], 1988, st 2177. W. Ried, M. Fulde and J.W. Bats, ,1989, 22, 969. P.O. Onys'ko, T.V. Kim, E.I. Kiseleva and A.D. Sinitsa, 2. Gen. Chem. W R m.Tranal.), 1989, %, 1129. V.V. Belakhov and B.I. Ionin, J. Gen. Chem. USSR -f Transl.), 1989, a, 1922. H. Koehler, L. Jaeger and D. Glanz, 8 . Chem., 1988, 28,

m,

at

29. 30. 31. 32. 33. 34. 35.

192. 36. 37. 38. 39. 40.

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a,

41. 42. 43.

m,

.

1756.

48.

T. Kappe, A. Pfaffenschlager and W. Stadlbauer, 1989, 666. H.J. Cristau, J. Kadoura, L. Chiche and E. Torreilles, Bull. SOC. Chim. Fr . I 1989, 515. A. Koziara, J. Prakt. Chelg 1988, 330, 473 (Chem. u )1989, , 7812d). A.R. Katritzky, J. Jiang and L. Urogdi, Tetrahedron Lgtt,, 1989, X I 3303. J. Barluenga, F. Lopez and F. Palacios, S Y I I ~ s 1989, ,

49.

J. Barluenga, I. Merino and F. Palacios, Tetrahedron

44. 45. 46. 47.

-,

u,

.,

298.

1989, X I 5493.

50. 51. 52. 53. 54. 55. 56. 57. 58. 59. 60. 61. 62. 63. 64. 65. 66. 67. 68.

69.

-

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2623511 Absf., 1990, u ,36821~). Lora, M. Carenza, G. Palma and P. Caliceti, padiat. EhyS. m . 1 1990, 117. 224. P. Wislan-Neilson, M: S. Islam and M.A. Schaefer, 8. S -icon, 1989, u, 135. 225. P. Wisian-Neilson and R. R. Ford, Nacrom olecules , 1989 , 22, 72. 226. P. Wisian-Neilson, M.S. Islam and T. Wang, a m . Mater. Sci. En%, 1 9 8 9 , dL 114. 227. P. Wisian-Neilson and M.S. Islam, b c r o m o l e c w , 1 9 8 9 , 22, 2026. 228. P. Wisian-Neilson, M.S. Islam and M.A. Schaefer, 8 , Sulfur S i l i c o n , 1 9 8 9 , a,135. 229. P. Widan-Neilson, M.S. Islam, S. Ganapathiappan, D.L. ,-m 1989, Scott, K.S. Krishan and R.R. Ford, 22, 4382. 230. P. Wisian-Neilson and M.A. Schaefer, mcromolecules. 1989, 22, 2003. 231. Y. Aoki, E. Watanabe and A . Imamura, T h e o m . , 1 9 8 9 , 57, 321. 232. M. Gleria, F. Minto, P. Bortolus, W. Porzio and A. Bologensi, Bur. Polvm. J., 1 9 8 9 , a,1039. 233. T. Masuko, R. Okuizumi, K. Yonetake and J.H. Magill, ,1 9 8 9 , 22, 4636. 234. M. Kojima and J.H. Magill, Polvmer, 1 9 8 9 , a,579. 235. D . R . Tur, V.S. Papkov, 1.1. Dubovik, D.Ya. Tsvankin, N.P. Provotorova, S.V. Vinogradova and G.L. Slonimskii, 1. S o e w Ser. B., 1 9 8 9 , Xl, 483 (aem. AbsS., 1 9 8 9 , u, 164688s). 236. V.G. Kulichikhin, E.K. Borisenkova, D.R. Tur, V.V. Barancheeva, 1.1. Konstantinov,,E.M. Antipov, V . E . Dreval and N.A. Plate, Vvsokomol. Soedin., Ser. A. I 1 9 8 9 1 111 1990, 37010k). 1636 (-St.. 237. E.M. Antipov, B.G. Krlichkhin, E.K. Borisenkova, D.R. Tur and N.A. Plate, Vvsokomol. Soedin.. Ser a c, 1 9 8 9 , 11, 2385 (aem. % 1 9 9 0 , u , 141473). 238. E.M. Antipov, S.A. Kuptsov, V.G. Kulichikhin, D.R. Tur and N.A. Plate,-ol. Chem.. Macrolaol. S v m I~ 1 9 8 9 1 261 69. 239. E.M. Antipov, V. G. Kulichikhin, L.K. Golova, N.P. Kruchinin, D.R. Tur and N.A. Plate, V d . Ser. A,, 1990, X I 108 ( m m . Abst., 1 9 9 0 , U2, 218626m). 240. N. saiki, Jpn. Kohai Tokkyo Koho, JP 01229811 (Chenr, BBBf;., 1 9 9 0 , u,100586~). 241. E.M. Antipov, V . G . Kulichikhin, E.K. Borisenkova, V.V. Barancheeva D R Turr and N.A. Plate, V Boedin.. Se;..A.; 1 9 9 0 , 12, 116 (Chem, I 19901 = I 199464~). 242. R.J. Ciora Jr. and J.H. Magill, Macromolecules, 1 9 9 0 , 23, 2350. 243. M. Kojima, D.C. Sun and J.H. Magill, Makromol. Chem., 1 9 8 9 , mI 1047. 244. M. Kojima and J. H. Magill, polvmer, 1 9 8 9 , 30, 1856. 245. R.J. Ciora Jr. and J. H. Magill, Macromolecul es, 1 9 9 0 , a,2359. 246. S . G. Young, M. Kojima and J.H. Magill, Polvm. PreDr. m. SOC. D iv. Polm. Chem.) 1 9 8 9 , 30, 2 2 5 (Chem. 1990, 3695311). 247. V . Percec, D. Tomazos and R. A. Willingham, Polvm. Bull., 1 9 8 9 , 22, 199. 223.

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8: Phosphazenes

34 I

248. R.E. Singler, R.A. Willingham, C. Noel, C. Friedrich, L. Bosio, E.D.T. Atkins and R.W. Lenz, polvm. PregL;,(a SOC. Div. Polvm. ChegL), 1989, a, 491 (Chem. BBBf;., 1990, U , 36511n). 249. M. Kojima and T. Son, Jpn. Kokai Tokkyo Koho, JP01051440 IChem.. , 1989, U,79056q). 250. A.A. Dembek, C. Kim, H.R. Allcock, R . L . S . Devine, W.H. Steier, and C.W. Spangler, a e m . Matar., 1990, 2, 97. 251. E.I. Rymtsev, I.N. Shtennikova, D.R. Tur and V.G. h . , FIg I 19891 LZi 72 (Chenr. Kulichikhin, pis'ma Z , 1989, 195820h). 252. D.R. Turn,G.I. Timofeeva, 2. Tuzar and S.V. Vinogradova, , -O S 1989, 32, 712 (Chem., 1990, u,140269a). 253. N.V. Vaail'eva, V.G. Kulichikhim, L.K. Golova, D.R. Tur, Soedin., S.V. Vinogradova and S.P. Papkov, 1 . Ser. 8 , 1989, U, 852 ( a e m . Abst,, 1989, U, 40303t). 254. T.H. Mourey, S . M . Miller, W.T. Ferrar and T.R. Molaire, Macromolecules, 1989, 22, 4286. 255. T.H. Mourey, S . M . Miller, W.T. Ferrar and T.R. Molaire, vm. Mater. Sci. Ena.,, 1989, a,353. 256. R.DeJaeger, D. Lecacheux and P. Potin, J. A m l . Pol= 1990, 2,1793. 257. D.N. Palmer, Pr-ctrochem. 245 SOC.. 1989, (Chem. m a . , 1990, U , 220310~). 258. P.W.M. Jacobs, J.W. Lorimer, A. Russer and M. Wasiucionek, J. Power Sourcm, 1989, 26, 483. 259. M.M. Lerner, L.J. Lyons, J. S. Tonge and D.F. Shriver, P r w . (Am. w. SOC.. Div. Polvm. Chepk), 1989, 4 3 5 (Chem., 1990, 8174r). 260. M.M. Lorner, L.J. Lyons, J.S. Tonge and D.F. Shriver, Chem. Ma-., 1989, 1, 601. 261. J.L. Bennett, A.A. Dembek, H.R. Allcock, B.J. Heyen and D.F. Shriver, Pr r. Bm. m. SOC.. Div. P o w 1989, X 5 7 (&. Abst.. 1989, U, 830811). 262. K.M. Abraham, M. Alamgir and R.K. Reynolds, L -tam. SOC., 1989, M I 3576. 263. K.E. Doan, S. Ganapathiappan, K. Chen, M.A. Ratner and D.F. Shriver, W e r . Res. SOC. S v m ~ . PrOC. I 19891 mi 343 ,-( 1989, 47088k). 264. N. Kajiwara, I. Kurachi, Y. Fukuyama, H. Wada, F. Odaka and H. Watabe, Jpn. Kokai Tokkyo Koho, JP01272635 (w &g&. , 1990, U .244294~). 265. T. Hirose, Y. Kamiya and K. Mizoguchi, J. ADD^. Polvm.

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m.)

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m., 1989,

s, 809.

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u,

.

(m.

(m.

u, u,

m,

u,

u,

Author Index

I n this index the number g i v e n in parenthesis is the Chapter number of the citation and this is f o l l o w e d b y the reference number or numbers of t h e r e l e v a n t citations within that Chapter

Aagard, O . M . (5) 82 Abaev, V.T. (1) 263, 264 Abdel-Rahman, N . M . (1) 138 Abdou, W.M. (1) 138, 139; (4) 14 Abdullina, N.A. (1) 105 Abe, J. (1) 193 Abe, K . (1) 303 Abe, N . (1) 149 Aberkane, 0 . (1) 297 About-Jaudet, E. (5) 101; (7) 67 Abraham, K . M . (8) 262 Abramov, V.Yu. (8) 31 Abramyan, T.D. (5) 110 Absalon, M . J . (6) 148 Abushanab, E. (6) 19 Achiwa, K . (1) 29, 30 Ackermann, E. (8) 24 Ackermann, M. (1) 246; (5) 93 Adamov, A.V. ( 5 ) 193 Adler, M.E. (7) 98 Affandi, S. (1) 72 Agarwal, K. (6) 237 Agrafiotis, D . K . (2) 10 Agrawal, S. (6) 120, 189, 190 Ahlert, K . (4) 63 Ahlrichs, R. (8) 7 Ahmad, A. (1) 283 Ahmad, W.-Y. (5) 126 Ahmed, S. ( 8 ) 96, 97 Ahn, K.4. (1) 39 Aitchison, K.A. (1) 59 Aitken, R.A. (7) 48 Akacha, A.B. (1) 83; (3) 8 Akai, H. (7) 38 Akega, M. (8) 82 Akekseiko, L . N . (8) 85

Akelah, A. (1) 301 Akita, H. (7) 108 Akiyama, T. (5) 15 Aksinenko, A.Yu. (1) 244 Aksnes, G. (3) 25 Aladzheva, I.M. (1) 291-294 Alajarin, M. (7) 117, 118; (8) 52-54, 56 Alamgir, M. (8) 262 Alario, F. (1) 297 Alberti, M. (8) 91, 119, 202 Alcaraz, J.M. (1) 79 Alcock, N.W. (1) 134, 419, 420 Aldenhoven, H. (1) 318; (4) 88 Aleinikov, S.F. (5) 133 Alewood, P.F. (5) 29 Al'fonsov, V.A. (8) 29 Ali, R. (2) 13 Alkubaisi, A.H. (8) 114, 115 Allcock, H.R. (8) 98, 99, 109, 117, 192, 209, 210, 215, 250, 261, 283 Allen, C.A. (8) 268 Allen, D.W. (1) 275 Aller, E. (8) 61 Al-Madfa, H.A. (8) 116 Alonso, E.O. (1) 295 Alovitdinov, A.B. (5) 165 Altenbach, H.-J. (7) 145 Altier, D . J . (8) 90 Alyea, E.C. (1) 179, 180 Amasaka, T. (8) 155 Amaudrut, J. (5) 195 Amri, K. (5) 108 Anderson, D.R. (5) 61 Anderson, C. (8) 9

343

Andrianarison, M. (1) 66, 67 Andrus, A. (6) 101 Angelov, C.M. (5) 194, 203, 216 Angelova, 0 . 1) 96; (7) 10 Angst, C. (5) 175 Angus, K . (6) 206, 207 Annen, U . (1) 448 Anthony-Cahil , S.J. (6) 92 Antipin, M.Yu. (1) 167, 292, 293, 336, 390; (5) 96; (8) 5, 13, 14, 68 Antipov, E.M. (8) 236-239, 241 Aoki, S. (5) 142 Aoki, Y. (8) 231 Appel, R. (1) 305 Arasappan, A. (7) 49 Aravamudan, G. (1) 250; ( 4 ) 27

Arbogast, B. (6) 133 Arbuzov, B.A. (1) 111-113, 115, 116, 157, 364, 365; (5) 97, 219 Archibald, R.S. (8) 117 Arendt, A. (5) 28 Arif, A.M. (1) 58, 375 Aristoff, P.A. (6) 231 Ariyoshi, S. (8) 123 Armstrong, R.W. (7) 139 Arques, A. (1) 166; (7) 122, 127; (8) 62 Arzumanyants, E . A . (1) 264 Asakura, T. (1) 358 Aseeva, R!M. (8) 164 Asseline, U. (6) 182

Atezhanova, G.O. (1) 75 Atkins, E.D.T. (8) 248 Atokhina, L.A. (5) 13 Atreyi, M. (6) 47 Atwood, J.L. (1) 55 Aubert, T. (8) 55, 63 Auer, M. (6) 34 Avasthi, K. (7) 100 Avens, L.R. (1) 118 Avery, T.L. (1) 444 Ayed, N. (1) 83; (3) 8 Ayrey, P.M. (3) 28 Baader, E. (3) 31 Baba, M. (6) 141 Babbit, P.C. (6) 38 Baccar, B. (1) 83; (3) 8 Baccolini, G. (1) 117, 446; (3) 13

Baceiredo, A. (1) 360, 366; (3) 46; (4) 34, 93, 94 Bachmeier , N. (6) 4 Backer-Dirks, J.D.J. (1) 59 Badri, M. (5) 56 Baechler, R.D. (1) 181 Baer, D.R. (8) 86 Bar, M. (8) 7 Baggiolini, E.G. (3) 35 Bagoutdinova, D.A. (5) 219 Bailar, J . C . (1) 12 Bailey, J.M. (6) 201 Baker, R. (5) 16, 17, 26 Bakker, C.G. (6) 72 Bakuradze, R.Sh. (8) 212

Balasubramanian, K.K. (1) 169, 170

Balegroune, F. (1) 213 Balgoblin, N. (6) 84 Balogh-Hergovich, E. (1) 160; (2) 33

Balueva, A.S. (1) 112, 115, 265

Balzarini, J. (6) 10, 141 Banbery, H.J. (1) 107 Banerjee, S. (7) 142 Bankmann, M. (1) 331, 410; (3) 27

Bankovskii, Yu.A. (1) 194 Banks, M.A. (1) 199 Banks, M . R . (5) 41 Bannwarth, W. (4) 40; (6) 62, 63, 209 Bansal, R.K. (4) 13 Bao, R. (5) 186 Baran, J. (7) 87 Barancheeva, V.V. (8) 236, 241 Baranov, A.P. (3) 15

Baranov, Yu.1. (1) 234 Barbato, S. (6) 66 Barcel6, D. (3) 5; (5) 72 Barluenga, J. (1) 284, 455, 456; (7) 24, 62, 63; (8) 42, 48, 49, 64, 65 Barnfield, E.A. (2) 8 Barrans, J. (4) 35 Barsegova, M.N. (1) 219 Barthelat, M. (2) 11 Bartmann, W. (3) 31 Barton, D.H.R. (5) 191; (6) 14 Barton, J.K. (6) 225 Bartsch, R. (1) 432-435; (8) 80 Basait, S . A . (6) 241 Batchelor, R.J. (1) 165; (8) 21 Bats, J . W . (8) 32 Battioni, J.P. (6) 139 Batyeva, E.S. (1) 189; (2) 2; (8) 29 Baudler, M. (1) 120-127 Bauer, S. (1) 340 Bauer, W. (1) 353; (7) 61 Baxter, S.G. (1) 414 Bazile, D. (6) 8 1 Bazin, H. (4) 64; (6) 183 Beachley, O.T. (1) 199 Beal, P. (6) 131 Beasley, V.R. (7) 136 Beau, J.-M. (7) 139 Beaucage, S.L. (4) 20; (6) 100 Beaucourt, J.-P. (1) 262; (7) 42, 43 Beck, G. (3) 31 Becker, G. (1) 65 Beer, P.D. (7) 140 Behl, H. (1) 290 Beijer, B. (6) 142 Beiter, A.H. (6) 53 Belakhov, V.V. (8) 34 Bell, A. (1) 39 Bellamy, F. (7) 28 Belletti, D. (1) 427 Below, P. (3) 31 Bel'skii, V.E. (5) 69 Belt, H.-J. (1) 184 Bel'tsova, T.G. (8) 144 Benac, B.L. (1) 58 Benevides, J.M. (6) 240 Bengstrom, M. (6) 192 Ben Jaafar, B. (2) 31 Benner, S.A. (4) 66; (6) 135, 154, 168, 169 Bennett, J.L. (8) 261 Bennett, M.A. (1) 132 Bentrude, W.G. (4) 17, 51; ( 6 ) 20

Berg, H. (6) 174 Bergamini, P. (1) 134, 202

Bergmann, A. (3) 31 Bergstrasser, U. (1) 413; (2) 34

Bergstrom, D. (6) 130, 131

Bernadou, J. (6) 7 Bernard, P.S. (5) 175 Bernardi, A. (7) 60 Bernardinelli, G. ( 7 ) 4 Bern&, J. (5) 89 Bertani, R. (8) 120 Bertrand, G. (1) 360, 366; (3) 46; (4) 93, 94

Besancon, J. (1) 40 Bespal'ko, G.K. (2) 49 Bestari, K. (8) 174, 291 Bestmann, H.J. (1) 289, 290; (7) 15, 50, 59

Bethel, D. (1) 162 Bhat, S.P. (6) 195 Bhattacharjya, A. (1) 147 Bhaumik, M. (1) 147 Biddle, J.A. (5) 142 Biedenbach, B. (1) 382 Bigge, C.F. (5) 173, 174, 176; (7) 78

Bihatsi-Karsai, E. (7) 115

Bildstein, B. (1) 63 Billington, D.C. (5) 16, 17

Bindig, U. (6) 175 Binger, P. (1) 377, 382 Birkel, M. (1) 377 Bittner, S . ( 8 ) 26 Bjergarde, K. (4) 68; (6) 127

Bjoerk, F. (8) 270 Blackburn, C. (7) 140 Blackburn, G.M. (6) 1 Blacker, J. (6) 229 Blanchard, L. (5) 175 Blank, I.B. (1) 263 Blanquet, S. (6) 31 Blaszczyk, J. (3) 32 Bleasdale, C. (6) 44 b a l , J.H. (5) 78; (6) 108

Bobde, V. (6) 47 Bobovski, T.P. (5) 176 Bock, H. (1) 331, 399, 410; (3) 27

Bode, U.K. (1) 220 Bodurow, C. (7) 131 Boeckman, R.K., jun. (5) 144; (7) 101, 102

Boese, R. (1) 319-321, 323, 324, 373, 374

Boganova, N.V. (1) 94;

345

Author Index

(2) 26; (4) 3, 4; (5) 139 Bohlen, R . (2) 51 Bohn, B.D. (1) 148; (7) 51 Boileau, S. (1) 297 Boisdon, M.T. (4) 35 Boizau, C. (6) 109 Boldaski, R. (7) 135 Bollen, A. (4) 60; (6) 191 Bologensi, A. (8) 232 Bolton, P.H. (6) 148 Bongartz, J.-P. ( 5 ) 126 Bonnet, J . P . (8) 288 Bonora, G.M. (6) 51, 68 Bookham, J . L . (1) 48 Books, J.T. (8) 220 Booth, P.M. (7) 103 Borai, V . N . (6) 5 Borch, R . F . ( 5 ) 77 Borden, W.T. (1) 385 Bordere, S. (8) 205, 214 Borer, B.C. ( 7 ) 90 Borer, P.N. (6) 77 Borisenko, A . A . (1) 6, 349, 350; (8) 66 Borisenkova, E.K. (8) 236, 237, 241 Born, M. (1) 297 Bornancini, E . R . N . (3) 26 Boros, P . (5) 113 Borowiecka, J . ( 5 ) 39 Borrmann, H. (1) 452; (7) 8 Bortolus, P. (8) 88, 232 Bosio, L. (8) 248 Bosyakov, Yu.G. (1) 75 Bott, S.G. (1) 55 Bottka, S. (6) 21, 22 Bou, A . (5) 124 Boubia, B. (7) 28, 30 Boucho, D. (5) 51 Bould, J . (1) 206 Boumendjel, A. (7) 75 Boutorine, A . S . (6) 139 Bowman, E. (5) 149 Bowyer, M. (1) 38 Boyd, E . A . (1) 4; (4) 10; (5) 105 Boyd, V.L. (5) 78 Bradford, V.S. (6) 232 Bradley, D.C. (1) 57, 59 Braga, D. (1) 428 Brahce, L . J . (5) 174 Brakel, C.L. (6) 118 Brandi, A. (3) 43, 44 Brandt, K. (8) 102, 290 Braun, M. (5) 120 Braunstein, P . (1) 213 Bremer, M. (1) 290 Brennan, D.J. (8) 117

Brenton, A.G. (6) 241 Breque, A . (1) 79 Bretsko, M.M. (8) 50 Breuer, E. (5) 201 Brevet, A. (6) 31 Brill, W.K.-D. (4) 70; (6) 125 Brint, P. (1) 206 Britten, J . F . (1) 269 Broder, S. (6) 108, 109 Brodesser, B. (5) 120 Broeders, N . L . H . L . (6) 238 Bronson, J . J . (5) 189, 190 Brooks, P.J. (1) 38 Broughton, H.B. (7) 103 Brovarets, V.S. (1) 285, 286 Brown, D.M. (6) 170, 171 Brown, D.W. (1) 198 Brown, J . M . (5) 226; (6) 86, 87 Brown, R . S . (1) 14 Brown, T. (6) 45 Briick, T. (1) 436 Brunden, M.J. (6) 74 Bruneau, C. (1) 192 Brunner, H. (1) 27, 95, 178; (3) 1; (7) 9 Brusilovskii, P . I . (1) 194 Bruvere, A. (1) 194 Bryce, M.R. (7) 81 Buchan, N . I . (1) 195-198 Buchanan, R.A. (3) 38 Buche, L. (8) 51 Buchko, G.W. (6) 167 Buchmann, B. (7) 99 Buchta, B. (5) 225 Buck, H.M. (5) 82, 214; (6) 238 Budzelaar, P.H.M. (1) 18, 42 Buisch, T . (1) 310 Bulpin, A. (4) 23; (5) 140, 141; (7) 82, 83 Bumber, A.A. (1) 263, 264 Bundel, Yu.G. (1) 152 Bungardt, D. (1) 319 Bunlov, A.R. (4) 91 Buono, G . (3) 42 Burangulova, R . N . (2) 37 Burgada, R . (2) 31, 42; (5) 138 Burilov, A . R . (1) 254; (4) 30, 31 Burn, A . J . (5) 70 Burnaeva, L . A . (2) 35-37 Burton, D.J. (7) 55, 56, 77 Burton, S.D. (2) 40

Busalev, Yu.A. (8) 81 Busch, R . D . (5) 170 Busch, T . (1) 337, 442; (4) 86; (8) 4 Busia, K. (5) 18, 25 Buwalda, P.L. (8) 285 Buzykin, V . I . (5) 197 Bykhovskaya? O.V. (1) 291, 292 Cabioch, J.-L. (1) 89, 90; (5) 122 Cadogan, J . I . G . (5) 41 Caesar, J . C . (2) 30; (4) 11 Caffyn, A . J . M . (1) 428 Cai, L. (1) 211 Cairns, S.M. (1) 255 Calderon, C.E. (5) 57 Caliceti, P. (8) 223 Callahan, L. (6) 237 Calogeropoulou, T. (5) 146 Cambell, T. (5) 175 Cameron, T.S. (8) 286-288 Caminade, A.-M. (1) 356, 362, 363; (4) 81; (5) 56; (8) 72 Carrmack, J.H. ( 7 ) 137 Camp, D. ( 1 ) 176 Cannavo, P. (3) 44 Cano, F.H. (7) 117; (8) 42 Capobianco, M.L. (6) 68 Caprioli, R.M. (5) 28 Carcuro, A. (6) 68 Carenza, M. (8) 223 Carey, J.V. (5) 226 Carless, H . A . J . (5) 18, 25 Carless, M. (5) 105 Carmichael, D. (1) 214 Carmichael, W.W. (7) 136 Carneiro, T.M.G. (1) 213 Carr, M.A. (7) 131 Carrera, P. (6) 65 Carrie, R . (1) 361, 367; (7) 13 Cartwright, J . S . (8) 275 Caruthers, M.H. (4) 54, 70; (6) 39, 115, 122, 125 Casey, C.P. (1) 26 Casida, J.E. (5) 74 Castera, P. (8) 105, 108, 287 Cavell, R.G. (1) 164, 165; (2) 50; (8) 21, 190, 191 Cazenave, C. (6) 109 Cech, D. (4) 63; (6) 160

346

Cech, T.R. (6) 94, 216 Cedergren, R.J. (6) 83, 93

Celander, D.W. (6) 216 Celentano, G. (7) 116 Celeries, J.P. (1) 287 Cen, W. (5) 132 Chabardes, P. (7) 133 Chabert, P. (7) 32 Chaddha, M. (6) 40 Chadha, A. (6) 233 Chadnaya, I.A. (1) 5, 6 Chai, M. (6) 207 Chaix, C. (6) 90 Chakrovarty, P.K. (5) 170 Chambers, R.D. (5) 127, 128

Chambrette, J.P. (8) 204, 205

Chambron, J.-C. (6) 225 Chamizo, J.A. (1) 437 Chandrasekhar, V. (8) 101 Chang, K. (5) 98, 106, 143; (7) 84

Chang, S.C. (8) 218, 219 Charandabi, M.R.M.D. (5) 163

Charrier, C. (1) 83, 355, 431; (3) 8

Charubala, R. (6) 107, 150, 151, 199

Chassot, L. (6) 222 Chattopadhyay, P. (1) 147 Chattopadhyaya, J . (6) 84, 132, 157

Chauzov, V.A. (1) 236, 237; (4) 36 Chavis, C. (6) 35 Cheh, A.M. (6) 233 Chehab, F.F. (6) 194 Chen, A. (7) 13 Chen, B.-C. (7) 57 Chen, C. (7) 39 Chen, J. (6) 31; (8) 280 Chen, J.-H. (6) 69 Chen, K. (8) 263 Chen, M. (5) 50 Chen, R. (5) 53, 185, 186, 221

Chen, S. (5) 156 Chen, S.J. (1) 215 Cheng, L. (5) 185 Cheng, M.-C. (1) 34 Cheon, S.H. (7) 139 Cherches, G.Kh. (8) 166, 167, 169

Cherkasov, R.A. (5) 136 Chernega, A.N. (1) 167, 325, 336, 390, 392, 397; (5) 96; (8) 5, 13, 14, 68 Chernov, A.N. (1) 189;

(5) 1 2 1

Chernova, A.V, ( 5 ) 183 Chest, V.P. ( 6 ) 181 Chi, D.Y. (6) 204 Chiba, M. (1) 29 Chiba, T. (1) 8 1 Chiche, L. (1) 277; (8) 45

Chida, N. ( 7 ) Chiesi-Villa, Chirkova, L.P. Chistokletov,

110 A. (1) 249 (1) 235

V.M. (2)

36, 37

Chivers, T. (1) 460; (8) 171-173

Chizhikova, 0.1. (8) 166 ChlGdek, S. (6) 91 Cho, B.S. (8) 118 Cho, S.K. (5) 160 Chojnowski, J. ( 5 ) 2, 223 Chopra, A.K. (7) 88 Chou, T.4. (7) 70 Chou, W.-N. ( 7 ) 3; (8) 10 Choukroun, R. (1) 363 Christ, W.J. (7) 139 Christau, H.-J. (1) 136, 276, 277; (7) 34; (8) 45 Christodoulou, C. (6) 86, 87 Christol, H. (1) 136 Chrnov, P.P. (2) 38 Chu, B.C.F. (6) 223 Chu, P.J. (1) 177 Chugunov, Yu.V. (4) 15, 24 Chung, Y.-C. (5) 66, 67 Church, K.M. (6) 235 Churusova, S.G. ( 5 ) 75 Cichy, A.F. (6) 19 Ciesla, J.M. (6) 23 Ciora, R.J., jun. (8) 242, 245 Cirule, M. (1) 194 Ciuffreda, P. (7) 129 Claesson, A . (5) 119 Clegg, W. (8) 22 Climent, M.S. (7) 26 Clyne, J. (6) 188 Coates, R.M. (5) 62 Coclizza, A.J. (4) 61 Coggio, W.D. (8) 98, 117 Cohen, J.S. (4) 62; (6) 102, 104, 105, 109 Colin, B. (6) 12 Collignon, N. (5) 101; (7) 67 Colman, R.W. (6) 201 Colombo, D. (1) 356; (4) 81; (7) 129; (8) 72 Colonna, F.P. (6) 51 Colston, J.E. (6) 196

Combs, P. (5) 170 Conda, L. (8) 112 Connolly, B.A. (6) 173 Conrad, P.C. (3) 38 Contreras, R. ( 2 ) 45 Coolidge, M.B. (1) 385 Cooper, M.K. (1) 92 Corbel, B. (5) 117, 145 Cordes, A.W. (8) 174, 175, 291

Corey, D.R. (6) 210 Corey, E.J. (7) 92, 105 Corless, M. (4) 10 Cory, M. (6) 236 Cosstick, R. (4) 72, 73; (6) 155, 156

Costello, C.E. (6) 222 Coughenour, L.L. ( 5 ) 174 Couret, C. (1) 389 Coutrot, P. (5) 158 Cowley, A.H. (1) 58, 317, 342, 375; (4) 89

Cox, M.B. ( 7 ) 141 Cramer, F. (6) 202 Cravador, A. (4) 60; (6) 191

Cregge, R.J. (7) 93 Cropper, P.E. (1) 275 Cruickshank, K.A. (6) 184 Csonka, G. (1) 439, 440 Cummings, D.G. (8) 268 Curtis, N.J. (I) 14 Cypryk, M. (5) 223 Czira, G. (5) 113 Dabkowski, W. (4) 76; (6) 114

Dahl, B.H. (4) 68; (6) 127

Dahl, 0. (4) 55, 68; (6) 127

Dahlem, A.M. (7) 136 Dahlhoff, W.V. (4) 39 Dake, L.S. (8) 86 Dakternieks, D. (1) 61 Dalpozzo, R. (1) 446 Damha, M.J. (4) 57, 65 Danheiser, R.L. ( 7 ) 74 Daniels, L.M. (5) 55 Danilov, S.D. (1) 234 Dare, H.F. (1) 381, 383 Dargatz, M. (3) 21 Darmuth, M. (1) 326 Dartiguenave, M. (1) 269; (4) 94

Dartiguenave, Y. ( 1) 269; (4) 94

Dartmann, M. (1) 313, 442 Darvich, M.R. (1) 136 Daumas, M. (7) 79 Davelaar, E. (5) 30

Author

Index

Davies, F.A. (7) 57 Davies, L.C. (6) 37 Davies, R.J.H. (6) 239 Davis, G. (8) 197 Davis, M.E. (1) 41 Davisson, V.J. (4) 48; ( 5 ) 34

Davtyan, A.G. (8) 216 Dawes, H.M. (1) 57 Dawson, M.I. (6) 176 Day, R.O. (2) 40; (5) 180, 181

Debart, F. (6) 137 de Boer, J.L. (8) 178 de Bont, H.B.A. (4) 44, 45

DeBruin, K.E. (5) 220 Debyser, 2. (6) 141 Decamp, D.L. (6) 201 De Clercq, E. (6) 10, 33, 141, 151

Declereq, J.P. (5) 57 Dedek, V. (1) 259 Deeming, A.J. ( 7 ) 40 Degols, G. (6) 208 Deinzer, M.L. (6) 133 DeJaeger, R. (8) 11, 74, 193, 204, 256

de Jesus, R. (5) 175 Dellaria, J.F., jun. (1) 135; (7) 12

Delmas, M. (5) 56; (7) 26, 72

Delorme, D. (7) 95 Dembek, A.A. (8) 215, 250, 261

Demuth, R. (1) 253 De Napoli, L. (6) 66 Dgn'e, G.Y. (8) 172 Deng, H.-B. (1) 252 Denis, J.M. (1) 90, 329, 330; (5) 122

Denmark, S.E. (7) 69 Denny, D.B. (1) 271 Dents, J.-M. (1) 89 DePoortere, M. (8) 219 Dervan, P.B. (6) 70, 71, 215

Deschamps, B. (1) 231, 412

Deschamps, E. (1) 418; (3) 10

Deschamps, R. (1) 409 Desmond, R. (3) 34 Desmyter, J. (6) 141 de Solms, S.J. (5) 16, 17 Despax, C. (4) 9 Desrosiers, P.J. (1) 2 1 1 Detsch, R. (1) 395 Deus, N. (1) 8 Deutsch, W.F. (8) 100 Devillers, J. (2) 11

347 Devine, R.L.S. (8) 250 Devon, T.J. (1) 10, 36 De Vos, M.-J. ( 4 ) 60; (6) 191

De Waal, B.M.F. (5) 82 Dewan, S.K. (5) 70 D'Halluin, G. ( 8 ) 11 Dhawan, B. (3) 7; (5) 116, 204

Dhindsa, A.S. (7) 8 1 Diefenback, U. (8) 103 Diel, P.J. (5) 169 Diemert, K. (1) 230 Dikshit, A. (6) 40 Dillon, K.B. (1) 279; (2) 13

Ding, M. (1) 21 Ding, X. (1) 300 Discher, S. (1) 155 Dissinger, S. (6) 196 Ditrich, K. (7) 104 Dixneuf, P.H. (1) 192 Dmitrichenko, M.Yu. (2) 23; (8) 28

Dmitriev, V.I. (1) 108 Doan, K.E. (8) 263 Dodge, J.A. (8) 210 Dobler, C. (1) 110 Dokuchaeva, I.S. (2) 36 Dolgushin, G.V. (8) 28 Dolinnaya, N.G. (6) 98 Dominski, Z. (6) 119 Domkowski, L. (5) 167 Dondoni, A. ( 7 ) 138 Donskikh, V.I. (1) 228, 245; (2) 23; (8) 28

Dorfman, Ya.A. (1) 103; (5) 8

Dormond, A. (1) 40 Dorokhov, V.I. (8) 50 Dorow, R.L. ( 7 ) 69 Dose, K. (6) 197 Dostalek, R. (7) 15 Douglas, T. (1) 423, 426 Downes, J.M. (1) 92 Downing, K. (6) 188 Downs, A.J. (2) 8 Doxsee, D.D. (8) 173 Doxsee, K.M. (3) 9 Doyle, T.W. (1) 171 Drach, B.S. (1) 285, 286 Draeger, M. (1) 389 Draheim, S.E. (7) 144 Drapailo, A.B. (1) 391 Dreef, C.E. (5) 168 Dreef-Tromp, C.M. (6) 46 Dreval, V.E. (8) 236 Dreyer, R. (1) 155 Driess, M. (1) 130 Drozdova, T.D. (5) 60 Drozdova, Ya.A. (1) 254; (4) 91

Drummond, J.T. (5) 173, 174, 176; (7) 78

Dubovik, 1.1. (8) 235 Duchamp, D.J. (6) 237 Duchenko, I.N. (2) 32 Duckworth, P.A. (1) 92 Dufour, N. (1) 356, 362, 363; (4) 81; (8) 72

Duhamel, L. (7) 133 Duhei, I.Ya. (6) 59 Duke, C.B. (8) 2 Du Mont, W.-W. (1) 182 Dunaway-Mariano, D. (5) 149

Dunbar, K.R. (1) 215 Duncan, L. (6) 206, 207 Dunn, S.F.C. (1) 162 Duplan, A.M. (6) 90 Dupre, D. (6) 139 Durand, G. (3) 5; (5) 72 Durst, H.D. (5) 66 Dutasta, J.P. (5) 57 Dvorakova, H. (6) 17 Dvornikov, A.S. (1) 159 Dybowski, P. (5) 35 Dylla, M. (1) 95; (7) 9 Dziewonska-Baran, D. (7) 87

Dziwok, K. (1) 82; (3) 4 Ebisuya, K. (4) 42; (5) 19

Edelmann, F.T. (4) 87 Edmundson, R.S. (8) 19 Edwards, M.L. (1) 173 Effinger, G. (1) 131 Efimov, V.A. (6) 59 Efremov, Yu.Ya. (1) 235, 364; (4) 16

Egan, W. (4) 20; (5) 78, 142; (6) 100, 108, 113

Egawa, T. (4) 80 Egorov, M.P. (1) 159 Eguchi, S. (7) 119, 120 Ehle, M. (1) 413; (2) 34 Eifert, G. (5) 113 Einstein, F.W.B. (1) 165; (8) 21

Eisenberg, R. (1) 209 Ejike, E.N. (1) 73 El Bakili, A. (8) 105, 106, 286, 287

El-Din, G.N. (1) 416, 417 Elekes, I. (5) 27 Eley, C.N. (5) 61 Elgadi, A. (5) 158 El Gaied, M.M. (5) 108 Elhaddadi, M. (5) 153 El Hamshary, H. (1) 301 Elias, A.J. (1) 167; (8) 176, 177

348

Orgunophosphorus Chemistry

Eliseenkova, R.M. (4) 32 Elkik, E. (5) 125 Ellermann, J . (1) 35; (5) 52

Elliot, D.J. (1) 207 Ellwood, S.B. (6) 44 El-Manouni, D. (2) 31, 42; (5) 138

El-Rahman, N.M.A. (4) 14 Elsevier, C.J. (8) 20, 188

Elmer, H.I.. (6) 218 Emanuilidi, S.E. (1) 263 Engel, R. (5) 91 Engelhardt, U. (5) 54; (8) 103

Engela, J . (1) 251; (4) 74, 75;

(6) 110,

158

Englard, S. (7) 142 Enholm, E.J. (7) 58 Enjalbert, R. (8) 289 Epiehina, T.A. (1) 241; (5) 5

Erabl, T. (3) 22 Erastov, O.A. (1) 111-116, 157, 265, 364, 365 Eritfa, R . (4) 54, 59; (6) 115 Erkelens, C. (4) 46 Ernst, L. (1) 261, 274 bcalc, R. (7) 94 Escudie, J. (1) 389 Eskew, N.A. (2) 17, 29 Eetrada-Yanez, H.R. (8) 182 Et-d-Hoghadh, G. (1) 351, 352 Eto, H. (5) 47, 48 Ettel, M.L. (5) 163 Evans, S . A . , jun. (2) 5, 17, 29 Exarhoa, G.J. (8) 90 Eya, B.K. (7) 91

Faaabender, F.J. (8) 77 Faucher, J.P. (8) 107, 108, 287

Federov, S.G. (8) 272 Fedorenko, T.V. (1) 1 Fedorov, S.B. (5) 69 Feher, M. (1) 120 Feng, H. (5) 112 Fenake, D. (1) 25 Ferguson, G. (1) 141, 142 Fernandes, J.R. (8) 89 Ferrar, W.T. (8) 254, 255, 280

Ferrero, M. (7) 62 Ferris, I.F. (8) 2, 90 Feshchenko, N.G. (1) 239 Featiaov, V.I. (5) 37 Fetter, J. (7) 130 Fidanza, J.A. (6) 103 Fiel, R.J. (6) 217 Field, L. (5) 73 Fife, T.H. (5) 65 Fild, H. (1) 227 Filonenko, L.P. (8) 67 Finch, R.A. (1) 444 Fincham, J.K. (8) 95 Fiacher, J . (1) 72, 420 Fischer, H. (2) 41 Fisher, K.J. (1) 179 Fisher, H. (8) 24 Fisher, H.H. (7) 107 Fittkau, S. (7) 73 Fleck, T.J. (2) 19; (7) 18

Flbrke, U. (1) 17 Flora-Vela, A. (3) 16 Floriani, C. (1) 249 Fluck, E. (1) 452; (7) 8 Focee-Focee, H.de la C. (7) 117; (8) 42, 54 Fbldesi, A. (6) 84 Fogagnolo, H. (7) 138 Foken, H. (4) 79 Fokin, A.V. (1) 236, 237; (4) 36

Facchin, G. (8) 120 Facklam, T. (1) 457 Fairley, T.A. (6) 236 Fait, J . (8) 171, 173 Faktor, M.M. (1) 59 Falck, J.R. (5) 20; (7) 30, 97

Fallouh, F. (1) 136 Fang, Y. (8) 111 Fanta, A.D. (1) 130 Fantin, G. (7) 138 Farina, V. (1) 172 Farnier, M. (8) 55, 63 Farooq, 0. (1) 240 Farrell, N.P. (6) 224 Farrow, S.N. (6) 10

Folkeason, B. (8) 9 Folkman, W. (6) 28 Fomina, E.A. (8) 169 Fontaine, X.L.R. (1) 206 Ford, M.J. (7) 103 Ford, R.R. (8) 225, 229 Forth, I. (8) 19 FOBS, V.L. (1) 349, 350; (8) 66

Foucard, A. (1) 402 Fournier, C. (8) 74 Fournier, J. (1) 192 Fox, C.M.J. (7) 103 Fraenkel, G. (1) 68 Frank, C.W. (8) 87 Franke, R . (2) 39; (5) 137

Franz, J.E. (5) 171 Frebel, H. (1) 320, 321, 323, 324

Frehel, D. (5) 124 Frejd, T..(l) 11 Freaneda, P.M. (7) 126; (8) 60

Frick, J.A. (5) 49 Friedman, A.E. (6) 225 Friedrich, C. (8) 248 Friedrich, D.M. (8) 86,

90 Friedricksen, B.P. (3) 14 Frigo, D.H. (1) 59 Frijns, J.H.G. (1) 18, 77 Fritz, G. (1) 128, 129 Froehlich, R. (1) 371 Fuchs, E.P.O. (1) 337 Fujii, H. (4) 56; (6) 60, 79 Fujikawa, K. (8) 154 Fujimoto, M. (8) 274 Fujimoto, T. (4) 42 Fujioka, H. (7) 139 Fujiwara, T. (4) 56; (6) 60, 214 Fukuyaoa, Y. (8) 264 Fulde, H. (8) 32 Furdon, P.J. (6) 119 Furmanova, H.V. (1) 200, 201

Furukawa, Furukawa, Furusawa, Furuyama,

1. (1) 149

M. (8) 217 0. (1) 298

E. (6) 76

Glirtner-Winkhaus , C. ( 1) 394

Gafarova, A.F. (1) 105 Gaffney, B.L. (6) 163 Gait, H.J. (6) 1 Gajda, T. (4) 17 Galakhov, M.V. (5) 130 Gallagher, M.J. (1) 38 Galluzzi, H.C. (5) 114 Galy, J . (8) 289 Gemper, H. (6) 205 Gamper, S. (1) 70 Ganapathiappan, S. (8) 229, 263

Ganem, B. (5) 14 Ganesh, G.N. (6) 186 Gao, L. (1) 21 Garanti, L. (8) 51 Garbed. A. (6) 51, 68 Garcia, C. (1) 276 Gareev, R.D. (8) 29 Gasc, M.B. (7) 34 Gaset, A. (5) 56; (7) 26, 72

Gaami, V. (2) 11

349

Author Index

Gaur, R.K. (6) 47 Gautel, M. (6) 34 Gautier, C. (6) 81 Gaynor, C. (6) 208 Gazizov, I.G. (5) 198 Gazizov, M.B. (5) 121 Gazizov, T.Kh. (1) 254; (4) 15, 24, 91

Gebel, W. (5) 43, 45 Gebhard, I. (6) 232 Geiser, T. (6) 101 Genet, J.P. (5) 159 Geoffroy, G.L. (8) 69 Geoffroy, M. (7) 4 Gerlt, J.A. (6) 148, 149 Gero, S.D. (5) 191; (6) 14

Gervais, D. (1) 363 Getman, T.D. (1) 252 Geue, R.J. (1) 104 Geyer, E. (1) 400; (5) 215

Ghazzouli, I. (5) 189, 190

Ghosh, D. (6) 241 Gibson, D. (5) 201 Gibson, V.C. (8) 22 Gierstae, R. (3) 25 Gildea, B. (6) 146 Gilham, P.T. (6) 74, 75 Gillam, I.C. (6) 179 Gillier, H. (2) 42 Gilyarov, V.A. (8) 16 Girard, J.P. (7) 94 Girard, Y. (7) 95 Glanz, D. (5) 44, 81; (8) 35

Glemarec, C. (6) 132 Gleria, M. (8) 88, 120, 232

Glidewell, C. (1) 141, 142

Gloer, K.B. (5) 146 Glowacka, D. (6) 198 Godovikov, N.N. (5) 96 Gold, B. (6) 235 Goldblum, A. (5) 201 Gol'dfarb, E.I. ( 8 ) 36 Gol'din, G.S. (8) 272 Golding, B.T. (6) 44 Golinski, J. (7) 87 Golokhov, D.B. (2) 22; (4) 25

Golova, L.K. (8) 239, 253 Golovan, E.B. (1) 6 Golovanov, A.V. (5) 133 Gomelya, N.D. (1) 239 Gonce, F. (1) 356; (4) 81; (8) 72

Goodchild, J. (6) 177 Goody, R.S. (6) 34 Gopalkrishnan, G. (6) 234

Gor, M. (1) 146 Gorchakov, V.V. (8) 85 Gorgues, A. (5) 56 Gorn, V.V. (6) 82 Gorshunov, I.Yu. (1) 189 Goryunov, E.I. (5) 11, 12 Gosney, I. (5) 41, 70 Gottsegen, A. (7) 115 Gough, G.R. (6) 74, 75 Gouygou, M. (1) 351, 352 Grabowski, S. (6) 29 Grachev, M.K. (4) 19 Graczyk, P. (3) 15 Graf, W. (7) 5 Graffeuil, M. (8) 108, 287

Grajkowski, A. (4) 67; (6) 153

Grandi, G. (6) 65 Grandjean, D. (1) 213 Granier, M. (3) 46 Grant, P.G. (6) 201 Grapov, A.F. (5) 75 Grassi, M. (5) 114 Gray, G.A. (1) 419 Gray, G.M. (1) 37 Gree, R. (1) 262; (7) 42, 43, 113, 114

Green, D.L.C. (5) 49 Green, L.M. (1) 31 Greenlee, W.J. (5) 170 Gregg, M.R. (1) 247; (4) 77

Grekov, L.I. (1) 103 Grelet, D. (1) 136 Griffith, M.C. (6) 92 Griffiths, D.V. (2) 30; (4) 11

Griffiths, P.A. (2) 30; (4) 11

Grigoryan, N.Yu. (1) 78 Grimaldo Moron, J.T. (1) 87

Grison, C. (5)'158 Grobe, J. (1) 253, 312, 313, 332-335,

371

Grobelny, D. (4) 6 Groebke, K. (6) 145 Grohmann, A. (1) 156 Grossmann, G. (5) 225 Grosspietsch, T. (1) 313 Gruber, M. (1) 119, 246; (4) 96, 97; (5) 93

Grueger, C. (7) 5 Grutzmacher, H. (1) 272, 273, 344, 345, 360; (3) 46; (4) 33, 93; (7) 65 Gryaznov, S.M. (6) 159 Gryaznova, 0.1. (6) 98 Gu, R.-L. (3) 33 Guastini, C. (1) 249

Gubnitskaya, E.S. (5) 166 Gudat, D. (1) 372 Guerch, G. (8) 288 Guesnet, J.-L. (6) 140 Gueth, W. (1) 442 Guida, W. (5) 175 Guilard, R. (8) 55, 63 Guillemin, J.C. (1) 329, 330

Guillemont, J. ( 7 ) 133 Gullidge, P.M.N. (6) 227 Gunji, H. (7) 109 Guo, C.Y. ( 5 ) 129 Gupta, K.C. (6) 47, 181 Gusar', N.I. (5) 79, 80 Gusarova, N.K. (1) 108, 109

Guy, P.M. (6) 243 Guybitg, K. (8) 20 Ha, H.-J. (4) 7; (5) 152 Ha, T.K. (8) 3 Habadie, N. (1) 269 Habicher, W.D. (4) 18 Habus, I. (1) 22, 23 Haegele, G. (1) 246; (5) 93

Haelters, J.P. (5) 117, 145

Hagan, M.D. (6) 91 Haggerty, B.S. (1) 426 Hagiwara, S. (7) 119 Hagnauer, G.L. (8) 197 Hahn, J. (1) 121, 123 Haikal, H.F. (6) 35 Hala, T. (6) 32 Halford, M.H. (6) 96 Hall, C.D. (1) 271 Halpern, J. (1) 211 Halterman, R.L. (1) 24 Ham, W.-H. (7) 139 Hambley, T.W. (3) 37 Hametin, J. (1) 354 Hammond, G.B. ( 5 ) 147; (7) 141

Hamor, T.A. (1) 107 Han, F. (6) 237 Hanack, M. (1) 257; (7) 11

Hanafusa, T. ( 7 ) 20 Hanaya, T. (5) 118 Handa, Y. (1) 91 Hanna, M.M. (6) 196 Hanson, B.E. (1) 41 Hanssgen, D. (1) 318; (4) 88 Hara, E. (8) 57 Haralimbidis, J. (6) 206, 207

Hargeave, P.A. (5) 28 Harger, M!J.P. (5) 206,

3io 207

Harlow, R.L. (1) 20 Harmat, N.J.S. (3) 29 Harris, F.M. (6) 241 Harris, R . K . (8) 80 Harris, R.L.N. (4) 8 Harris, T.M. (6) 234 Harrison, K . N . (1) 212 Harrison, P.J. (3) 30 Hartmann, H.-M. (1) 65, 441

Hartung, H. (3) 21 Harusawa, S. (5) 85-87 Hasegawa, Y. (6) 52 Hasenbach, J . (1) 121 Hashimoto, S. (1) 149; (8) 71

Hashizume, N. (3) 22 Hassanein, M. (1) 301 Hassler, K . (1) 60, 387 Hata, T. (4) 56; (6) 60 Hatakeyama, S. (3) 36 Hatanaka, M. ( 7 ) 33 Haupt, H.-J. (1) 17 Hawkins, L . D . (7) 139 Hayakawa, S. (6) 41 Hayakawa, Y. (4) 41; (6) 42, 43, 50, 85

Hayashi, A . (5) 99; (7) 85

Hayashi, T. (1) 9 Hayashi, Y. (8) 149 Hayes, J.A. (6) 74, 75 Haynes, R.K. (3) 37 Hays, S . J . (5) 176 Hearst, J.E. (6) 204 Heathcock, C.H. (7) 71 Hecht, G. (1) 95; (7) 9 Heckmann, G. (1) 452; (7) 8

Hecquet, B . (8) 74 Hegemann, M. (1) 332 Heimer, N.E. (5) 73 Heine, J . (1) 396; (2) 39; (5) 131, 135

Heinicke, J. (1) 102, 439, 440; (5) 115

Heintz, R . A . (1) 133 Heitz, M.-P. (1) 151, 153 Helbing, R . ( 4 ) 26 Helene, C. (6) 139 HeliGski, J . (5) 71 Helmut, S. (6) 228 Henkel, T. (8) 185, 186 Hensel, R . (1) 182 Herbst, H. (6) 64 Hercouet, A . (1) 256 Herdewijn, P . (6) 150, 151

Hermann, E. (8) 79 Hermesdorf, M . (1) 377 Hernandez Cano, F. (8) 54

Herne, J . (5) 58 Herrema, J.K. (8) 178 Herrmann, E. (8) 202 Herrmann, R. (1) 8; (6) 4 Hess, N.J. (8) 90 Hessell, E.T. (1) 16 Heuer, L. (1) 220, 221, 232, 274

Heung-Cho, P. (5) 83 Hey, E. (1) 62, 64 Heydt, H. (1) 337, 377, 457

Heyen, B.J. (8) 261 Hida, M. (4) 80 Hidaka, T. (5) 148 Hietkamp, S. (1) 226 Higgins, S . J . (1) 183 Hilali, S. (8) 74 Himdi-Kabbab, S. (1) 354 Himeda, Y. (7) 33 Hinman, L.M. (1) 74 Hirao, I. (6) 52, 80 Hiraoka, K . (8) 150, 151 Hirashima, A . (5) 47, 48 Hirata, K. (3) 22 Hiroi, K . (1) 193 Hirose, M. (6) 85 Hirose, T. (8) 265 Hitchcock, M.J.M. (5) 189, 190

Hitchcock, P.B. (1) 214, 433-435

Hobbs, P.D. (6) 176 Hodge, P. (1) 2 Hodgson, P.K.G. (5) 41 Hohn, A . (1) 104 Hoffmann, H. (3) 19 Hoffmann, R.W. (7) 104 Hogarth, G. (1) 205 Hojo, M. (1) 9 Holah, D.G. (1) 207 Holl, M.M. (1) 39 Holmes, J.M. ( 2 ) 40 Holmes, M . A . (7) 107 Holmes, R . R . (2) 40 Holt, M.S. (1) 419 Holy, A . (5) 192; (6) 17, 18

Holzappel, W . (7) 145 Holzl, W. (1) 368 Honda, K. (4) 53 Honda, T. (8) 71 Hong, S. (5) 143; (7) 84 Hoogerhout, P. (6) 46 Hoover, J . F . (1) 270; (7) 44

Hopkins, P.B. (6) 185, 219, 220

Horenstein, B . A . (7) 143 Horn, H.G. (1) 187 Horn, T. (6) 187, 188 Hornback, W.J. (7) 49

Horne, D . A . (6) 70 Horner, L. (1) 400; (4) 38; (5) 215

Hosoya, I. (8) 139 Hosseini, M.W. (6) 229 Houard, S. (6) 191 Houten, B.V. (6) 224 Hovanec, J.W. (5) 66 Hovard, S. (4) 60 Howard, J.A.K. (1) 381, 383

Howard-Lock, H.E. (1) 15 Hoye, P.A.T. (1) 212 Hrncir, D.C. (1) 56 Hruska, F.E. (6) 167 Hsi, J.D. (7) 31 HSU, L.-Y. (1) 252 Hu, D. (1) 380 Hu, S. (5) 53 Huang, H.-C. (7) 105 Huang, Y.-Z. (7) 22, 39 Huff, J.R. ( 5 ) 16, 17 Huffman, J.C. (7) 49 Huffman, J.H. (5) 163 Hughes, A.N. (1) 207, 222; (3) 17; (5) 180, 181 Hummel, M. (6) 64 Hurley, C.H. (6) 232 Hurst, G.D. (6) 205 Hursthouse, M.B. (1) 57, 59 Hussain, B. (1) 59 Hussain, W. (1) 107 Hustedt, E.J. (6) 185 Huszthy, P. (1) 146 Hutchings, D.S. (1) 19 Hutchinson, A.J. (5) 175 Hutchinson, D.W. (5) 102; (7) 86 Huy, N.H.T. (1) 415

Ibraimova, Zh.U. (5) 8 Ichida, H. (1) 13 Igau, A . (1) 360, 366; (4) 93

Ignat'ev, Yu.A. (1) 296 Ignat'eva, S.N. (1) 112, 364

Ignatov, M.G. (8) 81 Iida, A. (3) 11; (5) 107 Iino, Y. (7) 123 Iizawa, T. (1) 304 Iizuka, K. (5) 83 Ikai, K. (3) 11 Ikeda, M. (8) 155 Ikeda, S. (4) 80 Ikegami, S. (8) 71 Ikeuchi, T. (6) 120 Il'in, E.G. (8) 81 Il'ina, M.N. (8) 269

Author Index I l n o , Y. (8) 57, 59 I l ' y a s o v , A.V. ( 1 ) 189; ( 5 ) 121, 183 Imagawa, T. (8) 82 Imai, S. (5) 148 Imaki, N. (1) 93 Imamoto, T. (1) 88 Imamura, A. ( 8 ) 231 Imbach, J.-L. (6) 35, 81, 137, 138, 141 Imbeaux, M. (5) 125 Imhoff, P. (8) 20, 188 Inamoto, N. (1) 311, 314, 357; (3) 6; ( 5 ) 178 Inanaga, J. (1) 91 Indzhikyan, M.G. (1) 78; (5) 110 Inoguchi, K. (1) 30 Inomata, K. (1) 302 Inoue, K. (8) 123-125 Iocono, J.A. (6) 146 I o n i n , B.I. (5) 123, 205; (8) 34 Ionkin, A.S. (1) 364, 365 I r i b a r r e n , A. (6) 142 I s a a c s , N.S. (1) 416, 417 Ise, T. ( 1 ) 28 Ishchara, T. (5) 59 I s h i , S. (7) 146 I s h i d o , Y. (6) 52 Ishiyama, T. ( 7 ) 109 Ishmuratov, A.S. ( 5 ) 37 Islam, M.S. (8) 224, 226229 I s s l e i b , K. (1) 429, 430 I t o , T. (8) 276-278 I t o , Y. (1) 9 Ivanov, A.N. (1) 241 Ivanov, B.E. (5) 69 Ivanov, S.A. (4) 28 Ivanov, Yu.V. (8) 8 5 Ivanova, V.N. (5) 197, 198 Iverson, P.L. ( 6 ) 102 Ivonin, S.P. (1) 223 Iwai, S. (6) 240 Iwase, R . (6) 32 Iyer, R.P. (4) 20; (5) 142; (6) 100, 108 I z s o , G. (1) 146 Jachow, H. (1) 120, 125 J a c k , A.G.C. ( 5 ) 41 Jackson, J . A . (5) 146, 147 Jackson, R.H. (5) 175 Jackson, S.A. (7) 14 Jackson, W.R. (1) 216 Jacob, P. (6) 4 Jacobs, €I. (8) 92

35 1 Jacobs, P.W.M. (8) 258 Jacobson, R.A. (5) 55 Jacoby, D. (1) 249, 287 J a c q u i e r , R. (5) 153 J a g e r , L. (5) 43-45, 81; (8) 35, 96, 97 Jahngen, E.G.E. (6) 243, 244 Jahngen, J . H . (6) 243 J a i n , J.K. (4) 13 James, K. (4) 10; ( 5 ) 105 Janca, J. (8) 202 Jand, J. (8) 8, 104, 106, 181 J a n e c k i , T. (7) 135 Janoschek, R. (1) 309 Janssen, R.A.J. (5) 82 J a o u h a r i , R. ( 5 ) 127, 128 Jaud, J. (1) 447; ( 4 ) 82; ( 5 ) 56 Jaworska, M.M. (6) 106, 111 J e d l i n s k i , Z. (8) 102 Jeganathan, S. (1) 3; (7) 21 Jegorov, A. ( 1 ) 217 J e k e l , A.P. (8) 178, 290 J e n d r a l l a , H. (3) 31 J e n k i n s , A.M. (6) 241 J e n k i n s , C.L.D. ( 4 ) 8 J e n k i n s , I.D. (1) 176 Jennings, M.C. ( 1 ) 428 Jeong, B.D. ( 8 ) 161 Jeong, J. (7) 5 J e r i n a , D.M. ( 6 ) 233 J e u l a d e , M.-P. ( 7 ) 76 J i , Y. (6) 209 J i a n g , J. (7) 64; (8) 47 J i a n g , M.Y. (6) 93 J i a n g , X. (5) 164 Jideonwo, A. (1) 7 3 J i n , H. ( 7 ) 139 J i n a , A.N. (6) 176 J i r i k o w s k i , G.F. (6) 180 Johns, R.B. (4) 43; ( 5 ) 29 Johnson, D. (4) 59 Johnson, D.M. (5) 220 Johnson, D.R. (6) 198 Johnson, G. (5) 173, 174, 176; (7) 78 Johnson, P.D. ( 6 ) 231, 232 Johnston, L.J. (1) 295 Jones, A.S. (6) 10, 96 Jones, C.J. (1) 107 Jones, N.M. (6) 12 Jones, P.G. (1) 119, 220, 261; (4) 96 Jones, R.A. (1) 55, 58; (6) 163 Jones, S.S. (6) 8 6 , 88

Jones, T.K. ( 3 ) 34 Jordan, M. (4) 38 Joseph-Nathan, P. ( 2 ) 45 J u a r i s t i , E. ( 3 ) 16 Juge, S. ( 5 ) 159 Jungell-Nortamo, A. ( 6 ) 192 Junk, P.C. ( 1 ) 19 J u t z i , P. (1) 315 Kabachnik, M.I. (1) 238, 291-294; ( 3 ) 15; (5) 10-12, 60, 96, 177; (8) 4 3 Kabachnik, M.M. ( 1 ) 5 , 6; (5) 184 Kachkovskaya , L. S ( 1) 401; (8) 30 Kadel, J. ( 8 ) 180 Kadoura, J. (1) 277; (8) 45 Kadow, J.F. (1) 171 Kadyrov, A.A. (5) 130 Kadyrov, R. ( 1 ) 102; ( 5 ) 115 Kadyrova, V.Kh. (1) 105 Kaiser, K. (6) 175 Kajiwara, M. (8) 126, 196, 266 Kajiwara, N. (8) 146, 152, 165, 264, 276-278 Kajtar, M. ( 5 ) 100 Kajtar-Peredy, M. (1) 146; (7) 115, 130 Kalabina, A.V. (1) 245 Kal'chenko, V . I . (8) 27 Kallenbach, N.R. (6) 69 Kallmiinzer, A. (1) 449 Kalnik, M.W. (6) 164, 165 Kamaike, K. (6) 52 Kamaletdinova, R.N. (2) 35 Kamalov, R.M. (8) 36 Kamata, K. (8) 59 Kamer, P.C.J. (4) 2 I (6) 99 Kamiya, Y. (8) 265 Kamiyama, S. (8) 93 154, 217 Kan, Y.W. (6) 194 Kaneti, J. (1) 96; 7) 10 Kang, S.H. (7) 139 Kanoh. S. (1) 260 K a n o i t a , N.-(7) 124; (8) 58 Kant, M. (4) 26 Kanzaki, M. (3) 22 Kaplan, B.E. (4) 59 Kappe, T. (8) 44 Kaptein, R. (6) 239 Karaman, R. (5) 201

.

3s: Karasik, A . A . (1) 111, 113, 114, 116, 157 Karataeva, F.ICh. (5) 136 Kardanov, N.A. (5) 96 Kargin, Yu.M. (1) 296 Kariko, K . (6) 107 Karimov, K.R. (5) 165 Karino, H . (1) 81 Karl, R. (5) 90; (6) 3, 4 Karsch, H.H. (1) 69, 70 Kaseman, R. (6) 226 Kasukhin, L.F. (1) 167; (8) 13, 14 Katahira, M. (6) 240 Kato, H. (4) 41; (6) 41, 50 Kato, M. (6) 42 Kato, N . (5) 84 Kato, T. (1) 304 Katritzky, A.R. (7) 64; (8) 47 Katsuta, M. (8) 201 Katsutoshi, K . (8) 71 Katti, K.V. (1) 164, 165; (8) 21, 190, 191 Kaushik, M.P. (5) 163, 202 Kawabata, H. (6) 214 Kawasaki, T. (7) 35 Kawashima, T . (3) 6; (5) 178 Kazakov, P.V. (5) 103 Kazakov, V.P. (2) 18 Kazantseva, M.V. (1) 228, 245 Kazmierczak, K. (1) 124 K e l l , B. (6) 121 K eller, K. (4) 87; (8) 185 Keller, T.H. (7) 111 K eller, U . ( 1 ) 70 Kellner, K . ( 5 ) 115 Kellner, R . (1) 102; (3) 19 Kelly , J.E. (8) 280 K elly , R.C. (6) 232 Kemp, B.E. (5) 29 Kemp, T . J . (1) 202 Kennedy, J . D . ( 1 ) 206 Kennepohl, D.K. (2) 50 Kenyon, G.L. (6) 36, 38 Kesseler, K . (3) 31 Kettani, A.E.-C. (6) 7 Kezdy, F. (6) 237 Khabbass, N.D.A. (1) 279 Khachatryan, R . A . (1) 78 Khairullin, R.A. (5) 121 Khamatova, Z.M. (5) 183 Khambay, B . P . S . (7) 88 Khan, M.R. (4) 51; (6) 20 Khandker, M . N . I . (1) 283 Kharchenko, A . V . (1)

223; (8) 38 Khaskin, B.Q. (5) 37 Khasnis, D.V. (2) 48 Khawli, L.A. (5) 126 Khidre, M.D. (1) 139 Khizbullin, F.F. (5) 162 Khodaei, M.M. (1) 162 Khodah, A . A . (8) 16 Khotinen, A . V . (5) 97 Khristov, V . (5) 203 Khustnutdinova, E.K. (2) 35 Kibardin, A.M. (1) 453, 454 Kibler-Herzog, L. ( 6 ) 121 Kidd, K.B. (1) 58 Ki el basi n sk i , P. (3) 32 Kim, C. (8) 250 Kim, C.U. (5) 188, 190; (6) 15, 16 Kim, D.H. (8) 118 Kim, S. (1) 266, 288; (5) 55; ( 7 ) 25 K i m , S.S. (1) 266 Kim, T.C. (1) 403; (4) 85; (8) 8 K i m , T.V. (5) 208-210; (8) 33 K i m , Y.C. (1) 288; (7) 25 Kim, Y.J. (5) 160 Kimura, I. (8) 150, 151 Kimura, Y. (1) 298, 299 King, T . J . (8) 19 Kinoshita, K . (8) 125 Kinting, A . (1) 49, 110 Kirchgiisaner, R. (8) 92 Kirchmeier, R.L. (5) 129, 132 Kirchner, J . J . (6) 185 Kireev, V.V. (8) 2 6 Ki ri l ov, E.M.G. (1 96; (5) 76; (7) 10 Ki ri l ov, M. (1) 96 (7) 10 Kirpichnikov, P.A. 105 Kisarova, L.I. (1) 263, 264 Kiseleva, E.I. (5) 208-210; (8) 33 Kishi, K . (1) 9 Ki sh i , Y . (7) 139 Ki si el owski , L. (1) 289; (7) 59 Ki tas, E.A. (4) 43 Kitayama, M. (8) 122, 128-136, 138, 140, 160 Kliimer, F.-G. (1) 422 Klein, E. (1) 388 Klein, M. (6) 4 Kleinpeter, E. (3) 21 Klepa, T.I. (8) 12

Klinge bie l, U . (1) 66, 67; (8) 180 Klings te dt, T. (1) 11 Klobucar, W.D. (8) 220, 221 Klos ins ki, P. (5) 92 Kluge, H . (1) 448 Klumpp, E. (5) 113 Kniezo, L. ( 5 ) 89 Knight, G.J. (8) 271 Knoch, F. (1) 35; (5) 52 Knochel, P. ( 7 ) 70 Knoll, F. (1) 305 Knox, S.A.R. (1) 205 Knuppel, P.C. (1) 317; (4) 89 Kobayashi, E. (8) 84, 93, 94 Kobayashi, K . (8) 127 Kobayashi, Y . (6) 240; (7) 80 Koch, P . (1) 121, 122; (5) 200 Kohler , H . (5) 43-45, 81; (8) 35, 96, 97 Koenig, M. (1) 351, 352 Konig, T. (4) 18 Konig, W.A. (1) 178; (3) 1 Koguchi, Y . (7) 109 Koidan, G.N. (1) 242, 243, 346-348; (8) 38-40, 67 Koike, T . (1) 267 Kojima, M. (8) 234, 243, 244, 246, 249 Kojima, S. (3) 6; (5) 178 Kolbe, A . (8) 96 Kole, R. (6) 119 Kolesnik, N.P. (1) 101 Kolesnikov, S.P. (1) 159 Kolich, C.H. (8) 220 Koll, B. (2) 41 Kolleck, V . (1) 145; (7) 37 Kolodyazhnyi, 0.1. (1) 98, 200, 201; (2) 22; (4) 25 Kolova, E.V. (8) 272 Komarova, N.I. ( 6 ) 82 Komissarov, V . D . (2) 18 Komissarova, N.G. (7) 98 Komiyama, M. ( 5 ) 68; (6) 24-27 Komoda, Y . (4) 42 Kon, Y . (8) 127 Kondo, T. (1) 302 Kong Tho0 Lin, P.V.S. (6) 170, 1 7 1 Konieczko, W.T. (5) 4 Koning, T.M.G. (6) 239 Kononova, O.A. (5) 75

A ut hor I n d6lc.x Konopka,' A . (6) 120 Konovalova, I . V . (2) 35-38; (5) 6, 7 Konstantinov, 1.1. (8) 236 Koole, L.H. (5) 214; (6) 238 Koreeda, M. (7) 31 Korenchenko, O . V . (1) 244 Korkin, A . A . (1) 390; (2) 24; (8) 5, 6 Kormachev, V . V . (1) 234 Korolev, A.V. (1) 103 Korotaeva, N.M. (2) 18 Korshak, V . V . (8) 164 Korshin, E.E. (4) 16, 32 Kosar, W.B. (1) 198 Koschmieder, S.U. (1) 55 Koser, G.F. (4) 12; (5) 111 Koshushko, B . N . (5) 94 Kosolova, T . N . (8) 164 Kostyuk, A . N . (1) 100, 224 Kotek, R. (8) 145 K o u r i l , M. (8) 91, 119, 202 Kovalenko, L.V. (5) 103 Kovaleva, T . V . ( 2 ) 16; (8) 73, 78 Kovenya, V . A . (8) 68 Koyano, H. (5) 144 Kozarich, J . W . (6) 212, 213 Kozawa, H. (1) 281; (3) 24 Kozhushko, B . N . (5) 1 Koziara, A. (1) 150; (8) 46 Koziolkiewicz, M. (4) 67; (6) 108, 153 Kozlov, E.S. (1) 100, 223, 224 Kozlov, V . A . (5) 75 Kozmik, V . (1) 259 Kramer, B. (1) 394 Krauch, T. (6) 168 Krause, H.-W. (4) 79 Kravtsova, S.F. (8) 272 Krawiecka, B. (5) 224 Krebber, R. (1) 178; (3) 1

Krebs, B . (1) 313, 371, 442 Kreiter, C.G. (1) 379 Kreitmeier, P. (1) 359 Kremer, M. (1) 399 Krepyshevh, N.E. (2) 15 Kretschmann, M. (5) 44 K r i e g e r , C . (6) 34 Krishan, K.S. (8) 229 K r o l e v e t s , A.A. (5) 193

353 K r o l i k i e w i c z , K. (1) 148; (7) 51 Kron, V . A . (1) 228 Kropf, H. (3) 47 Kruchinin, N.P. (8) 239 Krug, A. (6) 160 Krutikov, V . I . ( 5 ) 133 Krzyzanowska, B. (5) 155 Ku, B. (5) 98, 106, 143; (7) 84 Kubelka, V. (1) 259 Kubo, I. (7) 9 1 Kubota, S. (8) 147, 148 Kuchen, W. (1) 230 Kudryavtsev, A.A. (8) 37, 40 Kudryavtseva, I.Yu. (5) 10, 11

Kudryavtseva, L.A. (5) 69 Kudzin, Z.H. (5) 151, 157 Kuehnel-Lysek, K. (1) 366 Kung, E. (4) 40; (6) 63 Kukhar, V . P . (1) 98, 167, 200, 201; (8) 13, 14 Kuksis, A. (1) 247, 248; (4) 77, 78 Kulagowski, J.J. (5) 16, 17, 26, 187; (7) 128 Kulak, T.I. (6) 9 Kulesha, I. (3) 35 K u l i c h i k h i n , V . G . (8) 236-239, 241, 251, 253 Kumar, A. (6) 10 Kumar, V. (6) 186 Kupchik, I.P. (1) 143 Kuptsov, S . A . (8) 238 Kurachi, I. (8) 264 Kurachi, Y . (8) 153 Kurahashi, A. (8) 113, 140, 143, 160 Kurihara, T . (5) 85-87 Kuroboshi, M. (5) 59 Kuroiwa, T . (5) 196 K u r t s , A.L. (1) 152 Kurukawa, M. (8) 201 Kusmierek, J.T. (6) 28 Kusumoto, T . (1) 88 Kuzmin, V.A. (1) 159 Kuznetsov, O.M. (7) 98 Kvasyuk, E.I. (6) 9 Kwon, C.-H. (5) 77 Kyogoku, Y . (6) 240 L a a l i , K. (1) 240 L a b a r r e , J.F. (8) 104-108, 286-289 L a b a u d i n i e r e , L. (2) 42 L a b e i t , S. (6) 34 Lachmann, J. (1) 69, 82; (3) 4

Lacombe, S. (1) 330 L a i , J.S. (1) 203 L a k h l i f i , T. (5) 195 Lakoba, I . S . (1) 219 L a l , K. (7) 100 Lalo, J. (5) 124 Lamande, L. (2) 43, 44 Lamberson, C.L. (6) 236 Lampeka, R.D. (1) 100 L a n c e l o t , G. (6) 140 Landgraf , B. (6) 4 L a n d i n i , D. (8) 112 Landry, S.D. (8) 282 h g , H. (1) 405-407 Lange, G. (1) 334 Langer, R.S. (8) 283 Langhans, P.K. (1) 51-54 Lanneau, G. (5) 223 Lao, Y . ( 7 ) 39 Laramee, J . A . (6) 133 Larsen, C . A . (1) 195-198 Larsen, S.B. (1) 444 L a s b a s t i d a , V. (3) 16 Laszkiewicz, B. (8) 145 h t i p o v , Sh.H. (1) 454 Lattman, M. (2) 48 Latypov, Z.Ya. (5) 13 Laude, B. (5) 195 Laurencin, C . T . (8) 283 L a u t e n s c h l a g e r , H.-J. (1) 27, 178; (3) 1 L a v r e n t ' e v , A.N. (5) 133 Lavrova, E.E. (8) 12 Lebedev, A . V . (4) 37; (6) 112, 116, 117 Lebedev, V . B . (5) 133 Le B i g o t , Y. (7) 26 Lebleu, B. (6) 107, 208 Lecacheux, D. (8) 256 Le C o r r e , M. (1) 256; (7) 46, 47 Le Doan, T. (6) 139 Lee, C . - S . (6) 232 Lee, P.H. (1) 266 Lee, S. (5) 149 Lee, S.J. (6) 240 Lee, S.W. (1) 137 Lee, V.M.-Y. (5) 27 Leeson, P.D. (5) 26 L e f k a d i t i s , D.A. (7) 36 Le Floch, P. (1) 338, 450; (7) 45 Le Floch, Y . (7) 113, 114 Le Gallic, Y. (7) 133 Le G o f f , P. (1) 421; (3) 12 Le G o f f i c , F. (7) 79 Le Guennec, M. (1) 329 Legusch, E.W. (5) 171 Lehn, J.-M. (6) 229 L e i s e , M. (1) 406, 407 h i s s r i n g , E. (1) 429,

353 430, 438

Lellouche, J.-P. (1) 262; (7) 42, 43

Lemaitre, M. (6) 208 Lemmen, P. (6) 4 Lempert, K. (1) 146; (7) 130

Lenders, J.-P. (4) 60; (6) 191

Leng, M. (6) 221 Lensink, C. (2) 46, 47; ( 5 ) 55

Lentz, R.R. (6) 244 Lenz, R.W. (8) 248 Leon, R. (4) 58; (6) 193 Leonetti, J.-P. (6) 208 Leont'eva, I . V . (1) 292-294

Leopold, D. (2) 7 Lepre, C . A . (6) 222 Lerner, M.M. (8) 259, 260 Le ROUX, J. (7) 46, 47 Leroux, Y. (2) 31, 42; (5) 138

Lesiak, K. (6) 33, 152 Lesnikowski, Z.J. (6) 106, 111

Leumann, C. (6) 145 Le Van, D. (1) 253, 312, 313, 332-335,

371 Levan'kov, S.V. (1) 97 Leveque, F. (6) 31 Levina, E.Ya. (1) 453, 454 Levina, L.V. (1) 103; (5) 8 Levison, B. (7) 100 Ley, S.V. (5) 24; (7) 103 Lhomet, G. (1) 287 Li, B.F.L. (6) 162, 164, 165 Li, S. (2) 12; (5) 50, 63, 211-213 Li, S.H. (1) 195-198 Li, S.W. (6) 107, 199; (7) 22 Lianis, P.S. (7) 36 Liao, Q. (5) 134; (7) 54 Liao, X. (2) 12; ( 5 ) 63, 211-213 Libermann, J. (8) 187 Liblong, S.W. (8) 171, 172, 175 Libonas, J. (8) 164 Lieser, B. (1) 120 Lilo, B. (5) 51 Lim-Chung, S. (1) 280 Lin, H.Q. (8) 203 Lin, I.J.B. (1) 203 Lind, R. (6) 131 Lindblad, E.B. (6) 218 Linden, A. (8) 286-288

Lindner, E. (1) 326 Lindner, H.J. (1) 187 Linehan, K. (3) 18 Ling-Chung, S. (7) 2 Liorber, B.G. (5) 183 Lipka, P. (5) 39 Lippard, S.J. (1) 39; (6) 222

Lipsom, S.E. (6) 204 Liskmp, R.M.J. (4) 44-46 Litinas, K.E. (7) 36 Liu, C.W. (1) 203 Liu, G. (1) 300 Liu, H.-J. (5) 88 Liu, L.K. (5) 50 Liu, M.-G. (1) 2 Liu, *R.S.H. (7) 89 Liu, S.-T. (1) 33, 34 Liu, X.P. (5) 42 Liuzzi, M. (6) 147 Livantsov, M.V. (1) 94; (2) 26; (4) 3, 4; ( 5 ) 139

Liverton, N . J . (5) 26 Lock, C.J.L. (1) 15 Lodaya, J.S. (4) 12; (5) 111

Lumin, S. (7) 97 Lumma, W.C., jun. (6) 242 Lunsford, J.H. (1) 177 Lutsenko, I.F. (1) 5, 6, 94, 349, 350; (2) 26, 28; (4) 3, 4; (5) 139, 184; (8) 66 Luu, B. (6; 209 Lyons, L.J. (8) 259, 260 Lyttle, M.H. (6) 77

Ma, Q.-F. (6) 36, 38 Ma, X. (5) 46

Ma, Y.-X.

(6) 122

McAleer, J.F. (7) 140 Macaudiere, P. (1) 79 McCaffrey, R.R. (8) 268 Maccarone, E. (1) 185 McCarthy, J.R. (1) 173 Maccioni, A. (8) 112 McClard, R.W. (7) 14 McCleverty, J.A. (1) 107 McDonald, J.F. (5) 171 McDowell, J.H. (5) 28 McElwee-White, L. (1) 161; (7) 41; (8) 23

Loecher, S.P. (8) 90 Lijschner, T. (1) 251;

McEwen, W.E. (1) 255;

(4) 74; (6) 110 Logunov, A . P . (1) 75 him, N.M. (1) 219 Loke, S.L. (6) 105 Lomakina, A.V. (5) 1 Lomonosov, A.V. (8) 272 Look-Herber, P. (1) 261 Lopez, A. (8) 53 Lopez, F. (1) 455, 456; (7) 63; (8) 42, 48, 64, 65 topusiihki, A. (5) 3, 4, 179 Lora, S. (8) 223 Lorcy, D. (7) 8 1 Lorenz, I.-P. (1) 131 Lorenzen, D. (1) 230 Lorenzo, A. (8) 6 1 Lorimer, J.W. (8) 258 Lough, A.J. (1) 142 Lu, H.-J. (1) 33 Lu, K.-L. (8) 69 Lu, X. (5) 109 Lu, Y. (3) 3 Lucas, A , , I11 (8) 157 Luczak, (5) 179 Ludeman, S.-M. (5) 78 Ludman, C.J. (1) 279 Ludwig, R. (1) 155 Luebke, K.J. (6) 71 Lucke, E. (1) 373 Luh, B.Y. (5) 188, 190; (6) 15, 16

McFadden, H.G. ( 4 ) 8 McFarlane, W. (1) 48 McGall, G.H. (6) 213 McGill, J.M. (7) 112 McGovern, J.P. (6) 232 McGrady, G.S. (2) 8 McGuigan, C . (4) 47; (6)

(2) 21; (7) 19

11-13

Macicek, J. (1) 96; (7) 10

Mack, D.P. (6) 215 McKenna, C.E. (5) 126

McKenna, E.G. (7) 29 Mchughlin, L.W. (6) 103, 146

Macomber, R.S. (5) 217, 218

McQueney, M.S. (5) 149 McWhorter, W.W., jun. (7) 139

Madak, A.S. (6) 86 Madden, H. (7) 88 Maeding, P. (3) 2 Miirkl, G. (1) 353, 359, 368, 449; (7) 61

Maffei, M. (3) 42 Maffrand, J.P. ( 5 ) 124 Mag, M. (4) 75; (6) 158 Magill, J.H. (8) 194, 199, 200, 233, 234, 242-246 Mahran, M.R. (1) 138, 139; (4) 14

Author

Index

355

Maia, A. ( 8 ) 112 Maier, L. ( 5 ) 169 Maigrot, N. ( 1 ) 355, 431 Maikuma, S. ( 4 ) 53 Maisano, F. ( 6 ) 65 Maizel, J. ( 6 ) 120 Majchrzak, M.W. ( 5 ) 157 Majewski, P. ( 1 ) 188; ( 5 ) 9 , 104

Majoral, J.-P.

( 1 ) 356, 362, 363, 402, 404, 447; ( 4 ) 81-84; ( 5 ) 56; ( 8 ) 7 2 , 181 Makhaeva, G.F. ( 5 ) 37 Makosza, M. ( 7 ) 87 Malavaud, C. ( 4 ) 35 Malito, J. ( 1 ) 180 Malone, T. ( 5 ) 174 Maloney, J.D. ( 1 ) 199 Malygin, V . V . ( 5 ) 37 Malysheva, S.F. ( 1 ) 108, 109 Mamedov, V . A . ( 1 ) 144 Mang, M.N. ( 8 ) 109, 215 Manitto, P. ( 7 ) 129 Manna, S . ( 7 ) 30 Manners, I. ( 8 ) 9 9 , 109, 209, 210 Manoharan, M. ( 6 ) 149 Manojlovic-Muir, L. ( 1 ) 428 Mansay, D. ( 6 ) 139 Marchenko, A.P. ( 1 ) 242, 243, 346-348; ( 2 ) 4 9 ; ( 8 ) 37-40, 67, 68 Marcoux, F.W. ( 5 ) 174 Marecek, J.F. ( 5 ) 22 Mariano, P.S. ( 5 ) 149 Marinas, J.M. ( 7 ) 26 Marinetti, A. ( 1 ) 338-341, 376; ( 7 ) 45 Markovskii, L.N. ( 1 ) 101, 306, 307, 325, 336, 391-393, 397, 401; ( 8 ) 27, 30, 31 Marron, B.E. ( 7 ) 96 Marsden, C.J. ( 2 ) 9 Marshall, A.S. ( 8 ) 280 Marth, C.F. ( 2 ) 20; ( 7 ) 17

Martin, J.C. (5) 188-190;

( 6 ) 1 5 , 16

Martin, S. ( 1 ) 312 Martinelli, M.J. ( 7 ) 139 Martynchik, S.P. ( 8 ) 169 Martynov, I.V. ( 1 ) 241, 244; ( 5 ) 5 , 37

Martynyuk, E.G. ( 8 ) 78 Maruyama, I. ( 8 ) 201 Maryanoff, B.E. ( 2 ) 4 Mashchenko, N.V. ( 1 ) 238; ( 8 ) 43

Massiot, G. ( 7 ) 75 Masson, S . ( 4 ) 23; ( 5 ) 140, 141; ( 7 ) 8 2 , 83

Mastryukova, T.A. ( 1 ) 238, 291-294; ( 5 ) 103; ( 8 ) 43 Masuda, I. ( 6 ) 52 Masuko, T. ( 8 ) 233 Mathey, F. ( 1 ) 7 9 , 214, 231, 338-341, 343, 355, 376, 408, 409, 412, 415, 418, 421, 424, 425, 431, 450; ( 3 ) 1 0 , 12; ( 7 ) 45 Matsuki, T. ( 8 ) 284 Matsukura, H. ( 7 ) 108 Matsukura, M. ( 6 ) 108, 109 Matsumoto, K. ( 8 ) 82 Matsumoto, Y. ( 6 ) 27 Matsuoka, Y. ( 5 ) 196 Matsura, A . ( 8 ) 279 Matsuura, T. ( 6 ) 214 Matsuura, Y. ( 1 ) 13 Matt, D. ( 1 ) 213 Matteucci, M. ( 6 ) 136 Matveev, E.D. ( 1 ) 152 Matzke, T. ( 1 ) 374 Mautz, D.S. ( 4 ) 4 8 ; ( 5 ) 34 Mavrin, G . V . ( 5 ) 198 Mawer, I.M. ( 5 ) 1 6 , 17 May, C.J. ( 1 ) 247, 248; ( 4 ) 7 7 , 78 Mayer, F. ( 1 ) 363 Mayer, R.B., jun. ( 6 ) 205 Mayer, U. ( 3 ) 19 Mayol, L. ( 6 ) 66 Mays, M.J. ( 1 ) 428 Mazidres, M.-R. ( 1 ) 402-404, 447; ( 4 ) 82-85; ( 8 ) 8 , 181 Mazumder, A . ( 6 ) 148, 149 Medvedeva, L.Ya. ( 8 ) 179 Meek, D.W. (1) 31 Meetsma, A . ( 8 ) 178, 285, 290 Meidine, M.F. (1) 372 Meier, G.P. ( 3 ) 38 Meijboom, N. ( 1 ) 42, 7 7 , 191 Meille, S.V. ( 8 ) 88 Meindl, P.E. ( 1 ) 248; ( 4 ) 78 Meinhold, H. (5) 36 Meisel, M. ( 1 ) 399 Mellin, T.N. ( 5 ) 170 Mel'nikov, N.N. ( 5 ) 75 Menu, M.-J. ( 4 ) 94 Mercer, S . ( 1 ) 161; ( 7 ) 41; ( 8 ) 23 Mercier, F. ( 1 ) 343,

408, 409

Mergardt, B. ( 7 ) 73 Merifield, E. ( 7 ) 132 Merino, I . ( 1 ) 284; ( 7 ) 24; ( 8 ) 49

Merker, R.L. ( 8 ) 200 Mertsulova, F.F. ( 5 ) 13 Merzweiller, K. ( 1 ) 25 Messeguer, A . ( 3 ) 5 ; ( 5 ) 72

Metternich, H.J. ( 1 ) 370 Meunier, B. ( 6 ) 7 Meyer, M. ( 8 ) 180 Meyer, U. ( 1 ) 315 Mezzina, E. ( 1 ) 117, 446; ( 3 ) 13

Michalska, M. (5) 39, 40 Michalski, J. ( 4 ) 7 6 ; ( 5 ) 4 , 40, 7 1 , 179; ( 6 ) 114 Midura, W. ( 5 ) 100 Mieloszynski, J.L. ( 1 ) 297 Miezere, R. (1) 194 Miftakhov, M.S. ( 7 ) 98

Mikhailopulo , I.A. (6) 5, 9

Mikhailov, I . E . ( 1 ) 263 Mikhailov, V.B. ( 1 ) 453 Mikhailov, Yu.B. ( 1 ) 453 Mikolajczyk, M. ( 1 ) 391; ( 3 ) 1 5 , 32; ( 5 ) 100

Mikulcik, P. ( 1 ) 69 Milhaud, P. ( 6 ) 208 Millard, J.T. ( 6 ) 219, 220

Miller, D.B. ( 7 ) 100 Miller, L.S. ( 1 ) 74 Miller, S.M. ( 8 ) 254, 255 Mills, J.L. ( 1 ) 118 Mills, S.G. ( 3 ) 34 Milosavljevic, E.B. ( 1 ) 420

Minami, T. ( 1 ) 80, 268; ( 5 ) 9 9 ; ( 7 ) 16, 85

Mindin, Ya.1. ( 8 ) 164 Minto, F. ( 8 ) 8 8 , 232 Mioskowski, C. ( 1 ) 151, 153; ( 7 ) 28, 30, 32

Mirkin, C.A. ( 8 ) 69 Mironov, V.F. ( 2 ) 3 8 ; (5) 6, 7

Miroshnichenko, V . V . ( 8 ) 37, 39, 68

Mirza, H.A. ( 1 ) 207 Mirzadegan, T. ( 7 ) 89 Misco, P.F. ( 5 ) 188, 190; ( 6 ) 16

Misra, K. ( 6 ) 40, 48 Mitchell, M.A. ( 6 ) 231, '232

Mitchell, T.N. ( 1 ) 184

3 56 Mitchell, W.M. (6) 107 Mitsuya, H. (5) 142 Mitter, F. (1) 387 Miura, H. (1) 9 Miura, K. (6) 52, 80 Miyemoto, T.K. (1) 13 Miyano, S. (5) 83 Miyaahi, T. (7) 80 Miyashita, A. (1) 81 Miyazaki, T. (7) 125 Miyoahi, K. (5) 196 Mizan, S. (6) 121 Mizoguchi, K. (8) 265 Mizrakh, L . I . (1) 282 Mizuno, M. (7) 139 Mlotkowska, B. (1) 175 Modak, A.S. (6) 87 Modro, T.A. (5) 64 Mohan, T. (1) 250; (4) 27 Moise, C. (1) 40 Mokrzan, J. (5) 151 Molaire, T.R. (8) 254, 255 Molchanova, G.N. (5) 60 Molin, H. (5) 119 Molina, P. (1) 166; (7) 117, 118, 121, 122, 126, 127; (8) 52-54, 56, 60-62 Molko, D. (6) 90 Moll, M. (1) 35; (5) 52 Moll, R. (5) 36 Mondeehka, D.M. (5) 194, 216 Monforte, J.A. (6) 204 Monoda, Y. (5) 19 Monteflorl, D.C. (6) 107 Montl, D. (7) 129 Montoneri, E. (5) 114 Moore, A.J. (7) 81 Moore, M. (6) 176 Moore, W.T. (5) 28 Moorhoff, C.M. (5) 64 Moreau, M. (5) 51 Morgan, T.K., jun. (6) 242 Mori, K. (4) 62; (6) 104, 105, 109 Mori, S. (8) 128-136, 138, 140, 141, 143, 156, 160 Morimoto, A. (8) 151 Morimoto, S. (8) 150 Morimoto, T. (1) 29, 30 Moroney, S.E. (6) 168, 169 Moro-oh, Y. (1) 208 MOrozova, L.N. (1) 100 Morris, R.E. (1) 204 Morse, K.W. (5) 163 Morvan, F. (6) 141 Moakva, V.V. (1) 233, 234

Orgon op hosp horus c'h em istn, Moss, G.P. MOSS, R.A.

(;{

z;,

67 Mostecky, J. (1) 259 Motoi, M. (1) 260 Motoki, S. (7) 125 Mouloungui, Z. (7) 26, 72 Mourey, T.H. (8) 254, 255 Mrozlk, H. (7) 107 Mualla, M. (5) 218 Miiller, C.E. (4) 22; (5) 38 Miiller, G. (1) 32, 69, 70, 82, 156, 158, 258, 451; (3) 4; (7) 5-7 Mueller, W.B. (8) 273, 282 Muhamnad, A. (1) 154 Mujumdar, A.N. (8) 199, 200 Mukhemetov, F.S. (4) 16, 32 Mukmeneva, N.A. (1) 105 Muller, E.P. (2) 41 Mullins, M.J. (3) 38 Munke, S. (3) 47 Munoz, A. (2) 43, 44 Munsey, M.S. (8) 110 Murehashi, E. (3) 41 Murashov, D.A. (8) 85 Muratom, S. (1) 260 Murillo, A. (2) 45 Murphy, D.E. (5) 175 Murray, W.T. (2) 29 Musin, R.G. (4) 30 Musin, R.Z. (1) 235, 454; (5) 121, 183 Mustaphin, A.H. (5) 97 Nabekawa, S. (1) 229 Nagai, H. (4) 56; (6) 60 Nagal, W. (1) 367 Nagalch, A.K. (6) 48 Nagano, K. (1) 81 Nagareda, K. (7) 20 Nagase, S. (7) 20 Nagata, R. (3) 40, 41 Nakada, Y. (8) 279 Nakahara, H. (8) 125 Nakamoto, A. (6) 78 Nakamura, H. (8) 123, 267 Nakamura, T. (1) 268 Nakane, M. (7) 125 Nakaniahi, K. (7) 143 Nakaniahi, T. (6) 144 Nakano, H. (4) 52; (6) 54 Nakata, M. (7) 139 Nakata, T. (7) 108 Nakayama, M. (1) 268 Nakazawa, H. (5) 196 N a , G.4. (4) 7; (5) 152 N m e , A. (6) 178

Namikoshi M 7) 136 Napier, J:J..($) 101 Narahara, T. (8) 158, 159 Natale, N.R. (8) 110 Navech, J. (4) 9 Nazmutdinova, V.N. (1) 235 Neckers, L. (6) 105 Neenan, T.X. (8) 283 Nefedov, O.M. (1) 159 Neganova, E.G. (1) 349, 350; (8) 66 Negrebetskii, V.V. (1) 293; (5) 75 Neijedly, Z. (6) 6 Neilaon, G.W. (6) 227 Neilson, R.H. (1) 4; (8) 75, 76 Nekhoroshkov, V.M. (1) 364; (4) 16 Nelson, J.H. (1) 72, 419, 420 Nelson, P.S. (4) 58; (6) 193 Nerker, R.L. (8) 199 Nesterov, L.V. (2) 15 Netzel, T.L. (6) 184 Neuman, A. (2) 42 Neuner, P. (6) 202 Newall, A.R. (1) 162 Newman, P.C. (6) 173 Newton, R.P. (6) 241 Nguyen, T.M. (8) 3 Nicolaides, D.N. (7) 36 Nicolaou, K.C. (7) 96 Niecke, E. (1) 310, 366, 369, 370, 372, 378, 388, 394-396, 442; (4) 86, 95 Nlef, F. (1) 424, 425 Nleger, M. (1) 310, 318, 378, 388, 394-396; (4) 86, 88, 95 Niel, G. (7) 94 Nlelsen, J. (4) 69; (6) 127, 128 Nlentledt, J. (1) 335 Nletzechmnn, E. (1) 102; (5) 115 Nlfant'ev, E.E. (4) 19 Nlitsu, T. (1) 311 Nlkltln, E.V. (1) 296 Nikltina, G.S. (8) 272 Nlkogosyan, L.L. (8) 166 Nlkolaeva, I . L . (4) 30, 31 Nikolaides, N. (5) 14 Nikonoror, K.V. (5) 13 Nikonov, G.N. (1) 112, 114-116 Nlnmons, H.L. (1) 24 Nlshiguchl, T. (1) 210

Author Index Nishii, K . (8) 279 Nishijlma, Y. (4) 52; (6) 54 Nishikawa, T. (8) 154, 217 Nishikova, N.G. (1) 152 Nishikubo, T. (1) 302-304 Nishioka, E. (1) 9 Nitta, M. (7) 123, 124; (8) 57-59 Nixon, J.F. (1) 214, 372, 432-435 Noble, N.J. (5) 33 Noel, C. (8) 248 Nogradi, M. (7) 115 Noguchi, T. (8) 201 Noh, S . K . (1) 133 Nohira, H. (1) 81 Noltemeyer, M. (1) 458; (8) 25, 182, 184, 187, 189 Nonaka, Y. (7) 35 Noren, C.J. (6) 92 Noren, J.O. (5) 119 Norman, N.C. (1) 375 Norval, E.M. (8) 80 Novak, P.M. (5) 176 Novikova, Z.S. (1) 5, 6; (2) 28; (5) 184 Nowick, J.S. (7) 74 Noyori, R. (4) 41; (6) 39, 41-43, 50, 85 Nozaki, H. (7) 146 Nuel, D. (7) 40 Numata, H. (3) 36 Nun, C.M. (1) 58, 317, 342, 375; (4) 89 Nuretdinov, I.A. (1) 144 Nuyken, 0. (8) 209, 210 Nuzillard, J.M. (7) 75 Nyangulu, J.M. (5) 88 Nyilas, A. (6) 84, 132 Nyulaszi, L. (1) 439, 440 Oae, S. (1) 281 Oakley, R.T. (8) 174, 175, 291 Oberhamner, H. (8) 180 Odaka, F. (8) 264 Odinets, I.L. (1) 238; (2) 28; (5) 103 O'Donnell, M.J. (7) 49 Oebels, D. (1) 422 Oehme, G. (1) 49 Ofitserov, E.N. (2) 38; (5) 6, 7 Ogilvie, K . K . (4) 65; (6) 83, 93 Oh, D.Y. (5) 98, 106, 143; (7) 84 O'Hagan, D. (5) 127, 128

357 Ohira, S. (7) 146 Ohira, Y. (8) 82 Ohms, G. (5) 225; (8) 79 Ohshima, Y. (6) 32 Ohta, H. (1) 267; (3) 22 Ohtsuka, H. (7) 35 Ohtsuki, M. (6) 56 Oishi, T. (7) 108 Oka, A. (4) 52; (6) 54 Okada, Y. (1) 80, 268; (5) 59 Okamoto, K . (8) 146, 152 Okamoto, T. (8) 93, 94, 154, 222 Okamoto, Y. (1) 358 Okamura, A. (5) 83 Okazaki, E. (3) 40 Okhlobystin, 0.Yu. (1) 263 Okude, K . (1) 13 Okuizumi, R. (8) 233 Okuma, K. (1) 267 Okuyama, T. (8) 153 Olah, G.A. (1) 240 Olders, E.A.T.A. (5) 214 Oleinik, V.A. (1) 242, 243, 346-348; (8) 39 O l m s , P. (8) 185 Olmstead, M.M. (1) 315 Omieljanczuk, J. (1) 391 Omori, H. (1) 208 O'Neill, J.K. (8) 275 Ono, M. (8) 158, 159 Onozawa, T. (1) 88 Ontsuka, E. (6) 240 Onys'ko, P.P. (5) 208-210; (8) 33 Oohasi, T. (8) 153 Opiela, S. (1) 123, 315 Opresnik, M. (5) 214 Or-, 0. (1) 405 Oretskaya, T.S. (6) 160 Orgel, L.E. (6) 95, 223 Ornstein, P.L. (5) 172 Orpen, A.G. (1) 18, 212, 375 Ortiago, J.F. (6) 180 Osaki, T. (5) 86 Osanai, K. (3) 36 Oshikawa, T. (5) 107 Oshiki, T. (1) 88 O m a n , F.H. (5) 180, 181 Ossig, E. (1) 326 Ostakhov, S.S. (2) 18 Otsuka, S. (1) 28 Otsuka, T. (7) 91 Ottenwaelder, H. (6) 226 Otvoe, L. (5) 27; (6) 161 Ovakimyan, M.Zh. (5) 110 Ovchinnikov, V.V. (5) 136 Ozaki, H. (4) 52, 53; (6) 54, 78, 129

Ozaki, S. (4) 42; (5) 15, 19, 23 Paetzold, E. (1) 49 Pagniez; G. (8) 205, 206, 213, 214 Pakrashi, S.C. (1) 147 Pakulski, M. (1) 342 Palacek, J. (1) 259 Palacios, F. (1) 284, 455, 456; (7) 24, 62, 63; (8) 42, 48, 49, 64, 65 Palazewski, K . (5) 28 Paliichuk, Yu.A. (5) 94 Palma, G. (8) 223 Palmer, D.N. (8) 257, 275 Palui, G.A. (1) 264 Palyutin, F.M. (1) 296 Pannell, L.K. (6) 233 Panosyan, G.A. (5) 110 Paoletti, C. (6) 81 Papkov, V.S. (8) 235, 253, 269 Paquer, D. (1) 297 Parc, G. (1) 297 Parente, D. (6) 65 Parish, R.V. (1) 73 Park, K.P. (4) 7; (5) 152 Parkes, H.G. (8) 114 Parra, M. (5) 24 Parsons, W.H. (5) 170 Parvez, M. (8) 99, 109 Paschalidis, C. (1) 32, 158, 258, 451; (7) 6, 7 Pasimourt, N. (8) 206 Paskevicius, R. (8) 164 Passerini, A. (1) 185 Pastor, S . D . (1) 16 Patalinghug, W.C. (1) 19 Patchett, A.A. (5) 170 Patel, D . J . (6) 164, 165 Paterson, M.C. (6) 147 Patois, C. (7) 68 Pauer, F. (8) 186 Pauli, J. (8) 81 Pautard-Cooper, A. (2) 5, 29 Pauwels, R. (6) 141 Pavlenko, N.V. (2) 14 Pavlov, V.A. (5) 183 Pechkovskii, V.V. (8) 166, 167, 169 Pedrini, P. (7) 138 Pei, D. (6) 210, 211 Pellerin, B. (1) 89, 330; (5) 122 Pellon, P. (1) 354 Peng, S.44. (1) 34 Pennington, W.T. (1) 56 Penny, S. (1) 15

35X

Percec, V. ( 8 ) 247 Peresypkina, L.P. (5) 166 Perez de Vega, M.J. ( 8 ) 53

Perich, J.W. ( 4 ) 43 Peringer, P. ( 2 ) 41 Perlikowska, W. ( 1 ) 391 Perlmutter, P. ( 1 ) 216 Perni, R.B. ( 7 ) 101 Perreault, J.-P. ( 6 ) 8 3 , 93

Pesheck, P.S. ( 6 ) 244 Pestana, D.C. ( 1 ) 386 Petersen, K.H. ( 4 ) 6 9 ; ( 6 ) 128

Petit, H. ( 1 ) 287 Petrov, A.A. ( 5 ) 123, 205 Petrov, G. ( 1 ) 96; ( 7 ) 10 Petrova, T.V. ( 5 ) 8 Petrovskii, I.L. ( 8 ) 43 Petrovskii, P.V. ( 1 ) 291-294;

( 5 ) 1 2 , 60 Petrus, C. ( 5 ) 153 Petrus, F. ( 5 ) 153 Petter, R.C. ( 7 ) 142 Petter, W. ( 2 ) 41 Peyman, A. ( 6 ) 97 Pfaffenschlager, A . ( 8 ) 44

Pfister-Guillouzo, G. ( 1 ) 330

Pfleiderer, W. ( 6 ) 4 9 , 53, 107, 150, 151, 199 Phillips, G.W. ( 1 ) 1 0 , 36 Phillips, L.R. ( 4 ) 20; ( 5 ) 142 Phillips, S.G. ( 8 ) 175 Phuong, P. ( 5 ) 126 Piccailli, G. ( 6 ) 66 Piccirilli, J.A. ( 6 ) 168 Pieles, U. ( 6 ) 202 Pieronczyk, W. ( 1 ) 9 5 ; (7) 9 Pietrusiewicz, K.M. ( 3 ) 20, 43-45 Pika, J. ( 6 ) 93 Pilichowska, S . ( 5 ) 155 Pilotti, M.U. ( 1 ) 381 Pinchuk, A.M. ( 1 ) 100, 242, 243, 346-348; ( 2 ) 49; ( 8 ) 37-40, 6 7 , 68 Pinsard, P. ( 1 ) 262; ( 7 ) 42, 43 Pirozhenko , V V. ( 1 ) 285, 286 Piteau, M. ( 1 ) 240 Pitt, H.S. ( 8 ) 7 Piven, V.A. ( 1 ) 219 Pla, F.P. ( 1 ) 271 Plass, W. ( 1 ) 452; ( 7 ) 8 Plate, N.A. ( 8 ) 236-239, 24 1

.

Plateau, P. ( 6 ) 31 Ple, G. ( 7 ) 133 Plgnat, F. ( 1 ) 136 Plyshevskii, S.V. ( 8 ) 166, 167

Podda, G. ( 8 ) 112, 121 Podsiadlo, S . ( 8 ) 211 Poirier, J.-M. ( 7 ) 133 Pokrovskaya, E.N. ( 8 ) 144 Polezhaeva, N.A. (5) 219 Polikarpov, Yu.M. (5) 177 Polonskaya, L.Yu. ( 1 ) 282 Polozhaeva, N.A. ( 5 ) 97 Polozov, A.M. (5) 97 Polushina, V.L. ( 1 ) 144 Pomerantz, M. ( 7 ) 3 ; ( 8 ) 1 0 , 26, 207, 208

Pompon, A . ( 6 ) 35 Pon, R.T. ( 6 ) 93 Ponomarchuk, M.P. ( 1 ) 167; ( 8 ) 1 3 , 14

Popov, A.G. (5) 193 Porizo, W. ( 8 ) 88 Porritt, G.M. ( 4 ) 7 1 ; ( 6 ) 123, 124

Porzio, W. ( 8 ) 232 Potapov, V.K. ( 6 ) 61 Potin, P. ( 8 ) 1 1 , 193, 204-206, 213, 214, 256 Potter, B.V.L. ( 5 ) 33 Potts, M.L. ( 8 ) 197 Poulter, C.D. ( 4 ) 4 8 ; ( 5 ) 34 Povolotskii, M.I. ( 1 ) 336, 392, 393, 401; ( 5 ) 210; ( 8 ) 30 Powell, D. ( 1 ) 130 Powell, J. ( 1 ) 247, 248; ( 4 ) 7 7 , 78 Powell, N.I. ( 7 ) 40 Power, P.P. ( 1 ) 315, 384, 386 Pownall, S . ( 6 ) 207 Pracejus, H. ( 4 ) 79 Prasad, G. ( 7 ) 58 Prestwich, G.D. (5) 22 Prihoda, J. ( 8 ) 79 Prikhod'ko, Yu.V. ( 1 ) 97 Prikota, T.I. ( 6 ) 5 Pringle, P.G. ( 1 ) 134, 202, 212 Prishchenko, A.A. ( 1 ) 9 4 ; ( 2 ) 26; ( 4 ) 3 , 4 ; ( 5 ) 139 Pritchard, C.E. ( 6 ) 45 Pritzkow, H . ( 1 ) 272, 273, 344, 345, 360, 380; ( 3 ) 4 6 ; ( 4 ) 33, 93; ( 7 ) 65 Probert, A.W. ( 5 ) 174 Prognayova, N. ( 8 ) 91 Provotorova, N.P. ( 8 )

212, 235

Pruitt, J.R. ( 7 ) 102 Puckette, T.A. ( 1 ) 10, 36 Pudovik, A.N. ( 1 ) 8 4 , 189, 235, 254, 453, 454; ( 2 ) 2, 35-38; ( 4 ) 30, 31, 9 1 ; ( 5 ) 6 , 7, 136; ( 8 ) 29 36 Pudovik, M.A. ( 1 ) 254; ( 4 ) 30, 91; ( 8 ) 36 Pujari, M.P. 5 ) 65 Pupeiko, N.E. ( 6 ) 5 Pykko, P. ( 2 ) 6

Qabar, M. ( 3 ) 39 Qing, W. ( 4 ) 7 6 ; ( 6 ) 114 Qiu, W. ( 5 ) 134; ( 7 ) 54 Qu, Y. ( 6 ) 224 Quaedflieg, P.J.L.M. ( 6 ) 238

Quartin, R.S. ( 6 ) 118 Quashie, S . ( 1 ) 375 Quassini, A. ( 8 ) 74 Quiclet-Sire, B. ( 5 ) 191; ( 6 ) 14

Quin, L.D. ( 1 ) 222; ( 3 ) 1 7 , 1 8 ; ( 5 ) 42, 180, 181

Rabow, L.E. ( 6 ) 148, 212, 213

Rademacher , P. ( 1 ) 442 Radics, L. ( 6 ) 21, 22 Ragulin, L.I. ( 4 ) 36 Rahmoune, M. ( 1 ) 361 Rahn, J.A. ( 1 ) 419 Raithby, P.R. ( 1 ) 428 Rakhmatulina, T.N. ( 1 ) 108, 109

Ramondenic, Y. ( 7 ) 133 Ranaivonjatovo, H . ( 1 ) 389

Randina, L.V. ( 5 ) 7 9 , 80 Rankin, D.W.H. ( 2 ) 8 Rano, T.A. ( 7 ) 110 Ransom, S.C. ( 6 ) 149 Rao, C.B. ( 1 ) 240 Rao, C.N.R. ( 8 ) 89 Rao, G. ( 7 ) 4 Rao, M.N.S. ( 1 ) 168, 250, 460; ( 4 ) 27

Rao, M.V. ( 6 ) 67 Rardon, D. ( 5 ) 217 Raston, C.L. ( 1 ) 19 Rathgeber, G. ( 6 ) 197 Ratner, M.A. ( 8 ) 263 Ratovskii, V.G. ( 8 ) 28 Raucher, S . ( 6 ) 220 Rault, I. ( 1 ) 354 Raundhill, D.M. ( 5 ) 76

Rausch, M.D. ( 1 ) 218 Raychaudhuri, S.R. ( 7 ) 100

Rayner, B. ( 6 ) 8 1 , 8 8 , 137, 138, 141

Raza, Z. ( 1 ) 22 Reamer, R.A. ( 3 ) 34 Rechencq, E. ( 7 ) 94 Reddy, N.S. ( 8 ) 101 Reddy, V.V.S. ( 1 ) 37 Redgrave, A.J. ( 5 ) 24 Rcdmill, K.A. ( 1 ) 37 Redmore, D. ( 3 ) 7 ; ( 5 ) 116, 204

( 6 ) 99

Roeschenthaler, G.V. ( 2 )

Reed, A.E. ( 2 ) 3 Reese, C.B. ( 4 ) 7 1 ; ( 6 ) 56, 67, 86-88,

Rippel, H.C. ( 7 ) 15 Robert, A. ( 7 ) 81 Roberts, J.D. ( 6 ) 224 Robertson, S.A. ( 6 ) 92 Robinet, G. ( 2 ) 11 Robins, R.K. ( 1 ) 444 Robinson, B.H. ( 6 ) 185 Robinson, G.H. ( 1 ) 56 Robles, D. ( 1 ) 8 Rockenbauer, A. ( 1 ) 146 Rodger, D.R. ( 5 ) 41 Roelen, H.C.P.F. ( 4 ) 2 1 ;

123, 124

Reffy, J. ( 1 ) 439, 440 Regan, A.C. ( 4 ) 1 0 ; ( 5 ) 105

Regan, J.B. ( 4 ) 20; ( 6 ) 100

Regitz, M. ( 1 ) 308, 337, 377, 379, 382, 398, 411, 413, 443, 448, 457; ( 2 ) 34 Reichenbach, N.L. ( 6 ) 107 Reitel, G.V. ( 1 ) 392, 393 Reiter, B. ( 1 ) 387 Reitz, A.B. ( 2 ) 4 Renner, G. ( 8 ) 209, 210 Rensch, 8. ( 3 ) 21 Repkova, M.N. ( 6 ) 8 2 , 143 Retherford, C. ( 7 ) 70 Reuter, J. ( 1 ) 128, 129 Revenko, G.P. ( 1 ) 75 Reynolds, M.A. ( 6 ) 36 Reynolds, R.K. ( 8 ) 262 Rhee, S. ( 6 ) 176 Rheingold, A.L. ( 1 ) 426; ( 8 ) 69 Rhodes, C.J. ( 1 ) 190, 316 Ribot, S.A. ( 5 ) 30 Ricard, L. ( 1 ) 7 9 , 214, 231, 338, 340, 341, 355, 421, 424, 425, 431, 450; ( 3 ) 1 2 ; ( 7 ) 45, 68 Richardson, J.F. ( 8 ) 172 Richter, W. ( 5 ) 9 0 ; ( 6 ) 3, 4 Rico, I. ( 5 ) 124 Ried, W. ( 8 ) 32 Rienhart, K.L. ( 7 ) 136 Riesel, L. ( 1 ) 145; ( 4 ) 26; ( 7 ) 37; ( 8 ) 81 Rife, J.P. ( 6 ) 112, 117 Rigby, J.H. ( 3 ) 39 Rihs, G. ( 1 ) 140 Riker, A.I. ( 6 ) 112 Riley, P.A. ( 6 ) 11-13 Riley, T.A. ( 1 ) 444

39, 51; ( 5 ) 58, 131, 135, 137 Roesky, H.W. ( 1 ) 458; ( 4 ) 87; ( 8 ) 1 , 25, 182, 184-187, 189 Rogers, R.D. ( 1 ) 199 Roget, A . ( 4 ) 6 4 ; ( 6 ) 183 Rokach, J. ( 7 ) 95 Rokhlin, E.M. ( 5 ) 130

Rokita-Trygubowicz, T. ( 5 ) 39

Rollin, P. ( 1 ) 174 Rolls, C.L. ( 1 ) 61 Romakhin, A.S. ( 1 ) 296 Romanenko, V.D. ( 1 ) 306, 307, 325, 336, 391, 393, 397, 401; ( 8 ) 5 , 30 Romanov, G.V. ( 1 ) 84 Roques, C. ( 1 ) 356, 402, 404, 447; ( 4 ) 81-84; ( 8 ) 7 2 , 181 Rosenberg, I. ( 5 ) 192; ( 6 ) 1 7 , 18 Rosenmeyer, H. ( 6 ) 174 Rosenthal, A. ( 4 ) 6 3 ; ( 6 ) 160 Rossi, E. ( 7 ) 116 Rossi, J.C. ( 7 ) 94 Rossi, R.A. ( 1 ) 50; ( 3 ) 26 Rossornondo, E.F. ( 6 ) 243 Rotello, V.M. ( 7 ) 106 Roth, A. ( 5 ) 170 Roth, D. ( 7 ) 50 Roth, H.J. ( 4 ) 22; ( 5 ) 38 Rott, N.T. ( 5 ) 62 Rozanov, I.A. ( 8 ) 8 5 , 179 Rozinov, V.G. ( 2 ) 23; ( 8 ) 28 Ruban, A.V. ( 1 ) 325, 336, 391-393, 397, 401; ( 8 ) 5 , 30 Rudkevich, D.M. (8) 27 Rudnitskaya, L.S. ( 1 ) 236, 237 Ruiz-Mazon, M. ( 1 ) 437 Rumpel, H. ( 5 ) 200

Running, J.A. ( 6 ) 188 Runova, O.B. ( 5 ) 21 Rusakov, V.A. ( 8 ) 272 Rusanov, V.M. ( 1 ) 234 Russell, M.J.H. ( 5 ) 226 Russer, A. ( 8 ) 258 Ryabov, B.V. ( 5 ) 123, 205 Rybkina, V.V. ( 8 ) 28 Rymar, V.T. ( 8 ) 166 Rymtsev, E.I. ( 8 ) 251 Ryzhikov, D.V. ( 8 ) 36 Ryzhikova, T.Ya. ( 1 ) 84 Rzepa, H.S. ( 7 ) 1 ; ( 8 ) 170

Saadein, M.R. ( 4 ) 5 1 ; ( 6 ) 20 Saalfrank, R.W. ( 8 ) 24 Sabatino, P. ( 1 ) 428 Sabio, M. ( 6 ) 242 Sabol, J.S. ( 7 ) 93 Sackett, P.H. ( 6 ) 244 Sadana, R. ( 6 ) 167 Sadanani, N.D. ( 5 ) 4 2 , 181

Safina, Yu.G. ( 5 ) 136 Safsaf, A. ( 2 ) 42 Sagandykova, R.R. ( 5 ) 8 Sagi, J. ( 6 ) 161 Sahi, T.A. ( 8 ) 124 Saiki, N. ( 8 ) 240, 284 Saito, I. ( 3 ) 40, 41; ( 6 ) 200, 214

Saito, T. ( 7 ) 125 Sakai, N. ( 8 ) 281 Sakama, T. ( 8 ) 165 Sakamoto, M. ( 7 ) 35 Sakamoto, N. ( 8 ) 146, 152 Sakatsume, 0. ( 4 ) 49, 50; ( 6 ) 55-57, 76

Sakhibullina, V .G. ( 5 ) 219

Sakulin, G.S. ( 5 ) 69 Sakuma, K. ( 7 ) 137 Salcedo, R. ( 1 ) 437 Sales, K.D. ( 1 ) 280; ( 7 ) 2

Salisbury, S.A. ( 6 ) 45 Sal'keeva, L.K. ( 4 ) 24 Sallin, K.J. ( 1 ) 135; ( 7 ) 12

Salornon, R.G. ( 7 ) 100 Samadi, M. ( 5 ) 191; ( 6 ) 14

Samuels, W.D. ( 8 ) 90 Sanchez, M. ( 1 ) 403, 404, 447; ( 4 ) 82-85; ( 8 ) 8 , 181 San'chez-Baeza, F. ( 3 ) 5 ; ( 5 ) 72 Sangen, 0. ( 4 ) 52; ( 6 ) 54

Organophosphorus C'hc.mi.siry

Sangokoya, S.A. (1) 56 Santacroce, C. (6) 56 Santiago, A.N. (1) 50 Sappa, E. (1) 427 Sarfati, S.R. (6) 178 Sargent, M.V. (7) 134 Sargeson, A.M. (1) 104 Sarin, P.S. (6) 120 Sarroff, A. (1) 38 Sasaki, S. (1) 357 Sasaki, Y. (1) 13, 80 Sasakura, T. (8) 149, 163, 168 Satge, J. (1) 389 Sathyanarayana, S. (6) 181 Satici, H. (7) 58 Sato, H. (7) 35 Sato, K. (1) 88 Sato, T. (1) 314 Sauer, H.E. (6) 197 Sauvage, J.-P. (6) 225 Savignac, P. (1) 99; (5) 101; (7) 67, 68, 76 Sawada, S. (6) 25 Sawai, H. (6) 30 Sawyer, J.F. (1) 204 Sayadyan, S.V. (1) 78 Sayer, J.M. (6) 233 Scahill, T.A. (6) 232 Scaiano, J.C. (1) 295 Schiifer, H.-J. (6) 197 Schaefer, M.A. (8) 224, 228, 230 Schiiufele, H. (1) 380 Schaffhaueen, J.G. (3) 38 Schanze, K.S. (6) 184 Schaumann, E. (7) 73 Scheide, G.M. (8) 75, 76 Scheldrick, W.S. (8) 183 Schelkun, R.M. (7) 70 Scheller, D. (3) 2 Scherer, O.J. (1) 327, 328, 436 Schiemann, A. (1) 371 Schier, A. (7) 5 Schirmer, W. (1) 17 Schlewer, G. (5) 21 Schleyer, P.von R. (2) 3, 10 Schlosser, M. (1) 3; (7) 21

Schloz, U. (8) 25 Schmaltz, T. (6) 130 Schmidbaur, H. (1) 32, 82, 156, 158, 258, 451; (3) 4; (7) 5-7 Schmidpeter, A. (1) 459; (8) 183 Schmidt, H. (1) 429, 430, 438; (2) 46, 47; (5) 55

Schmidt, H.-G. (8) 187 Schmidtchen, F.P. (6) 230 Schmuck, A . (2) 6, 7 Schmutzler, R. (1) 86, 119, 220, 221, 232, 246, 261, 274; (2) 27; (4) 29, 96, 97; (5) 93; (8) 80 Schnalke, M. (1) 123 Schneider, J. (1) 379 Schneider, K.C. (4) 66; (6) 135, 154 Schneider, L. (5) 175 Schneider, R. (1) 382 Schnochel, H. (8) 7 Schnurr, W. (1) 411, 443 Schoeller, W.W. (1) 310, 337, 442; (4) 86; (8) 4 Schollmeyer, D. (3) 21 Scholz, G. (1) 126, 127 Scholz, M. (4) 87 Scholz, U. (1) 457; (8) 182, 189 Schomburg, D. (1) 221, 232, 274 Schubert, F. (4) 63 Schultz, P.G. (6) 92, 210, 211 Schulze, J. (1) 313 Schwartz, A.W. (6) 72, 221 Schwartz, C.E. (3) 38 Schwarz, W. (1) 65 Schweitzer, C.T. (1) 204 Schwetlick, K. (4) 18 Scolaatico, C. (7) 60 Scott, B. (5) 129 Scott, D.L. (8) 229 Scremin, C.L. (6) 51 Sczakiel, G. (6) 34 Sedqui, A. (5) 195 Seega, J. (1) 246; (5) 93 Seela, F. (6) 174, 175 Seeman, N.C. (6) 69 Segall, Y. (5) 74 Seger, J. (8) 91 Seidl, S. (1) 60 Sekine, M. (4) 56; (6) 60, 73, 144 Sekini, M. (6) 32 Seliger, H. (6) 180 Seligsohn, H.W. (6) 117 Selim, A. (1) 301 Sella, A. (1) 204 Semenii, V.Ya. (8) 78 Semkina, E.P. (1) 84 Sene, A. (4) 23; (5) 140, 141; (7) 82, 83 Sennett, M.S. (8) 197, 198 Seppelt, K. (2) 6, 7 Serafinowska, H.T. (6) 87

Serhan, C.N. (7) 96 Seeeke, U. (8) 184 Seto, H. (5) 148 Seyden-Penne, J. (5) 199; (7) 65 Shaborova, Z.A. (6) 160 Shackleton, J.M. (6) 13 Shadid, B. (5) 30-32 Shagvaleev, F. Sh (1 ) 233, 234 Shahnazarian, N. (1) 179 Shaikhudinova, S.I. (1) 108 Shakhidoyatov, Kh.M. (5) 165 Shapoahnlkov, S.I. (8) 38 Sharifuuln, A.Sh. (1) 105 Sharipov, G.L. (2) 18 Sharma, D. (4) 13 Sharma, P. (6) 181 Shaw, B.L. (1) 183 Shaw, R.A. (8) 83, 95, 100, 114-116 Shcherbina, T.M. (5) 10, 12 Sheldrick, G.M. (1) 66; (8) 184-186 Shen, G.S. (3) 9 Shen, Y. (5) 134; (7) 23, 27, 52-54 Shereshovete, V.V. (2) 18 Sherman-Gold, R. (4) 58; (6) 193 Shermergonn, I.M. (8) 29 Shermolovlch, Yu.G. (1) 101, 143; (8) 31 Shevchenko, I.V. (1) 200, 201 Shi, L.-L. (7) 22 Shi, Y.B. (6) 204 Shibazaki, H. (8) 93, 94 Shigeo, M. ( 8 ) 113 Shih, T.L. (7) 107 Shih, Y.E. (5) 50 Shiina, A. (1) 304 Shima, K. (4) 92 Shimamura, C. (1) 260 Shimamura, J. (1) 81 Shimamura, K. (1) 260 Shimazu, M. (6) 30 Shimidzu, T. (4) 52, 53; (6) 54, 78, 129 Shimojo, M. (1) 304 Shinohara, K. (7) 146 Shinohara, T. (4) 42 Shinozaka, K. (6) 30, 105, 121 Shiomi, D. (1) 311 Shiozawa, N (1) 278 Shiuey, S.-J. (3) 35 Shlyapintokh, L.P. (8)

.

.

Author Index 169 Shokol, V.A. (5) 1, 94, 95 Shore, S.G. (1) 252 Short, R.L. (1) 59 Shreeve, J.M. (5) 129, 132 Shriver, D.F. (8) 259-261, 263 Shtennikova, I.N. (8) 251 Shugar, D. (6) 23 Shurubara, A.K. (5) 79 Shvets, V.I. (5) 21 Sibanda, S. (6) 86, 88 Siddique, R.M. (1) 186 Sidky, M.M. (4) 14 Sidorov, V.I. (8) 144 Sih, C . J . (3) 33 Sikanyika, H. (7) 140 Silina, E.B. (5) 95 Sills, M.A. ( 5 ) 175 Simon, E.S. (6) 29 Singer, B. (6) 28 Singh, D. (6) 186 Singh, R.K. (6) 40 Singler, R.E. (8) 87, 248 Sinisterra, J.V. (7) 26 Sinitsa, A.D. (2) 32; (5) 209, 210; (8) 33 Sin'ko, N.L. (8) 272 Sinyashin, O.G. (1) 189; (2) 2 Sinyashlna, T.N. (2) 38; (5) 6, 7 Sip, M. (6) 221 Slriwardane, U. (2) 48 Sitdikova, T.Sh. (1) 233, 234 Slvets, G.G. (6) 5 Skirl, R. (5) 44 Skoda, J. (6) 6 Skolirnowaki, J.J. (1) 222; (3) 17 Skowroiiska, A. (5) 35 Skowroiiska, R. (5) 151 Skrypczybski, 2. (5) 71, 222 Skuballa, W. (7) 99 Skuratovich, L.G. (8) 166, 167 Sladky, F. (1) 63 Slawin, A.M.Z. (7) 103 Sleiman, H.F. (1) 161; (7) 41; (8) 23 Slonimskii, G.L. (8) 235, 269 Smirnov, V. (4) 54; (6) 115 Smith, A. (5) 206 Smith, A.B., I11 (7) 110 Smith, L.M. (1) 57 Smith, M.B. (1) 212

36 1 Smith, S.J. (1) 247, 248; (4) 77, 78 Smith, T.D. (6) 205 Smolii, O.B. (1) 285, 286 Snatzke, G. (1) 23 Sobol, R.W. (6) 107, 199 Sokolov, M.P. (5) 197,

198 Sokolov, V.B. (1) 241, 244; (5) 5 Sokolova, M.E. (8) 169 Sokolova, N.I. (6) 159 Solouki, B. (1) 399 Solov'ev, A.V. (1) 101 Solujic, L. (1) 420 Sommer, H. (1) 226 Sonmer, V.B. (4) 68 Son, T. (8) 249 Sonnenberg, U. (1) 322 Sopchik, A.E. (4) 17, 51; (6) 20 Soroka, M. (5) 154 Sostero, S. (1) 134, 202 Sournles, F. (8) 104-106, 108, 286, 287, 289 Spahn, M. (1) 452; (7) 8 Spangler, C.W. (8) 250 Spaniol, T.P. (1) 383 Spasov, S.L. (5) 216 Speers, P. (1) 271 Speier, G. (1) 160; (2) 33 Spek, A.L. (8) 178 Speranza, G. (7) 129 Spiegel, G.U. (1) 85 Spielmann, H.P. (6) 204 Spless, B. (5) 21 Splnk, C.W. (1) 218 Sproat, B.S. (6) 142, 202 Stack, M. (1) 181 Stadelmann, W. (8) 80 Stadlbauer, W. (8) 44 Staley, D.L. (8) 69 Stalke, D. (1) 66, 67, 378; (4) 87, 95; (8) 185, 186 Stam, C.H. (8) 20 Stamatov, S.D. (4) 28 Staninets, V.I. (1) 143; (8) 31 Stankevich, I.V. (8) 212 Stannett, V.T. (8) 203 Stavinoha, J.L. (1) 10, 36 Stawinski, J . (4) 90; (6) 58, 126 Stec, W.J. (4) 67; (6) 102, 108, 111, 113, 153 Steglich, W . (5) 161 Steier, W.H. (8) 250 Stelgelmann, 0. (1) 32,

156, 158, 258, 451; (7) 6, 7 Stein, C.A. (6) 102, 104, 105, 109 Stein, H. (6) 64 Steinmiiller, F. (8) 183 Stelzer, 0. (1) 51-54, 85, 226; (8) 80 Stemerick, D.M. (1) 173 Stenberg, B. (8) 270 Stengele, K.-P. (6) 49 Stepanov, A.E. (5) 21 Stepanov, G.S. (8) 36 Stepanova, E.V. (1) 219 Stephm, H. (1) 345 Sternfield, F. (5) 24 Stevenson, K. (1) 181 Sting, P. (5) 161 Stirchak, E.P. (6) 133, 134 Stolarski, R . (6) 23 Stone, F.G.A. (1) 381, 383 Stone, M.P. (5) 73; (6) 234 Storm, C. (6) 108 Strada, A. (7) 116 Stradi, R. (7) 116 Stranln, B.P. (5) 162 Strazewski, P. (6) 172 Streitwleser, A. (2) 10 Streubel, R. (1) 369, 370, 378; (4) 95 Stringfellow, G.B. (1)

195-198 Stromberg, B. (5) 54 Struchkov, Yu.T. (1) 167, 263, 292, 293, 336, 390; (5) 96; (8) 5, 13, 14, 68 Stryker, J.M. (1) 270; (7) 44 Stubbe, J. (6) 148, 212, 213 Studnev, Yu.N. (1) 236, 237; (4) 36 Sturis, A. (1) 194 Sturtz, G. ( 5 ) 117, 145 Stutz, A.E. (7) 139 Su, D. (5) 129, 132 Su, W . 4 . (7) 92 Subasinghe, C. (4) 62; (6) 102, 104, 105 Subheendra Rao, M.N. ( 8 ) 176, 177 Subramanian, R.S. (1) 169, 170 Suda, H. (1) 260 Sugawara, T. (8) 158, 159 Sugeta, H. (6) 240 Sugiyama, H. (6) 200, 214 Suhadolnik, R.J. (6)

362 107, 199

Sulikowski, G.A. (7) 110 Sulkowski, W . (8) 216 Sumitomo, T. (8) 165 Summerton, J.E. (6) 134 Sun, D. (6) 120 Sun, D.C. (8) 243 Sun, W.-C. (6) 243 Sun, X. (3) 3; (5) 109 Sund, C. (6) 157 Sunjic, V. (1) 22, 23 Suriano, J.A. (1) 20 Sutter, P. (5) 200; (8) 41

Suwa, K . (1) 28 Suzuki, H. (1) 208, 298 Svara, J . (1) 51-53 Swamy, K.C.K. (2) 40 Swann, P.F. (6) 162, 164, 165

Swinson, J. (5) 73 Switzer, C. (6) 169 Swords, B. (4) 47 Symons, M.C.R. (1) 190 Syvanen, A.-C. (6) 192 Szameitat, J . (1) 381, 383

Szecsi, J . (6) 161 Szemo, A. (6) 161 Szewczyk, J. (3) 18 Szulagyi, J. (5) 113 Szymoniak, J. (1) 40 Taba, K.M. (4) 39 Tabone, J.C. (6) 205 Tabyaoui, B. ( 8 ) 55 Tachon, C. (1) 351, 352 Taguchi, S. (8) 274 Tajima, S. (7) 109 Takada, M. (1) 229 Takagi, M. (8) 123 Takahashi, A. (8) 158, 159

Takahashi, K. (8) 127, 162, 267

Takaku, H. (4) 49, 50; (6) 55-57, 76, 79 Takano, S. (3) 36 Takaya, H. (1) 81 Take, Y. (1) 208 Takechi, N. (5) 15 Takeishi, M. (1) 278 Takeshige, Y. (6) 24, 25 Takeuchi, H. (7) 119, 120 Takeuchi, K . ( 6 ) 27 Takeya, R . ( 5 ) 47 Takuma, Y. (1) 93’ Talamas, F.X. (7) 139 Talanov, V.S. (8) 31 Tamada, Y. (5) 107 Tamai, Y. (5) 83

Tamas, J . (1) 146; (7) 130

Tambute, A. (1) 79 T m , C. (6) 172 Tamura, Y. (8) 162 Tan, P.S.G. (5) 70 Tancheva, C.N. (5) 194, 216

Tancic, Z. (7) 4 Tand, C.W. (5) 220 Tand, Y. (5) 221 Tang, C. (5) 221 Tang, Y.-Y. (6) 189 Tangour, B. ( 4 ) 35 Tani, K. (1) 28 Tanigaki, T. (8) 123-125 Tanigawa, E. (1) 28 Taniguchi, M. (7) 139 Tao, X. (3) 3; ( 5 ) 109 Tarasova, R.I. (1) 233, 2 34

Tasdelen, E.E. (1) 216 Tassone, G. (1) 185 Tatsuno, Y. (1) 28 Tatsuta, K . (7) 109 Tay, M . K . (5) 101; ( 7 ) 67 Taylor, R.J.K. (7) 90 Teare, J . (6) 203 Tebbe, K.-F. (1) 120, 126 Tebby, J.C. ( 2 ) 30; (4) 11

Telser, J . (6) 184 Tenner, G.M. (6) 179 Te‘oule, R. (4) 64; (6) 90, 183 Ternansky, R.J. (7) 144 Teterevkov, A.I. (8) 169 Teulade, M.-P. (1) 99 Thakker, D.R. (5) 142 Thelin, M. (4) 90; (6) 58, 126

Thenappan, A . (7) 55, 56, 77

Theopold, K.H.

(1) 133, 423, 426 Thorn, G . L . (7) 48 Thomas, E.J. (7) 132 Thomas, G . J . , jun. (6) 240 Thompson, C.M. (5) 49 Thompson, S.K. (7) 7 1 Thoraval, J.Y. (1) 367 Thornton, D.M. (5) 102; (7) 86 Thornton-Pett, M. (1) 57, 206 Thorpe, F.G. (1) 2 Thuong, N.T. (6) 182 Tikhonenkova , N. E. (8) 272 Tikhonina, N . A . (8) 16 Tikhonov, V.P. (8) 12

Timofeeva, G.I. (8) 252 Timokhin, B.V. (1) 228, 245

Tinant, B. (5) 57 Tino, J.A. (7) 139 Tinofeev, A . M . (5) 96 Tiriicchhio, A . (1) 427 Tiripicchio Camellini, M. (1) 427

Titova, M . I . (1) 1 Tkachenko, O.V. (6) 9 Tmaas, J . (5) 113 Toda, F. ( 7 ) 38 Toia, R.F. (5) 74 Tokmoto, Y. (6) 32 Tollerfield, S.M. (6) 11, 13

Tolmachev, A . A . (1) 100, 223, 224

Tolstikov, G . A . (2) 18, (7) 98

Tomasz, J . (6) 21, 22 Tomazos, D. (8) 247 Tondelli, L. (6) 68 Tonge, J . S . (8) 259, 260 Tonnard, F. (1) 354, 361 Topal, M.D. (6) 166 Topiol, S. (6) 242 Topolski, M. (5) 167 Torgasheva, N . A . (5) 37 Torgomyan, A.M. (5) 110 Torkelson, S. (6) 176 Torreilles, E. (1) 277; (8) 45

Torrence, P.F. (6) 33, 152

Toscano, R . A . (1) 437 Toscano, V . G . (1) 295 Toth, I. (1) 41 Totschnig, K . ( 2 ) 41 Toulme, J . J . (6) 109 Toupet, L. ( 7 ) 113 Touzin, A.M. (5) 159 Toyota, K. (1) 358 Traverso, 0. (1) 134, 2U2 Tregear, G.W. (4) 43; (6) 206, 207

Trehan, A. (7) 89 Treichler, A. (5) 225 Tristin, Yu.G. (2) 36, 37 Troev, K . (5) 76 Trofimov, B.A. (1) 108, 109

Trogler, W.C. (1) 137 Trommer, W.E. (6) 197 Tsubokawa, M. (8) 122, 156

Tsuchiya, H. (1) 229 Tsukamoto, M . (1) 3; (7) 21

Tsukamoto, Y. (5) 99; (7) 85

363

Tsutsumi, H. (8) 155 Tsvankin, D.Ya. (8) 235 Tsvetkov, E.M. (2) 24; (8) 6 Tumas, W. (1) 20 Tupchienko, S.K. (2) 32 Tur, D.R. (8) 212, 235-39, 241, 251-53, 269 Turecek, F. (1) 217 Turner, G. (6) 45 Turner, M.A. (1) 15 Turner, M.L. (1) 205 Turro, N.J. (6) 225 Tutunjian, P.N. (1) 177 Tuzar, Z. (8) 252 Tzschach, A. (1) 102, 106; (5) 115; (8) 70 Ubasawa, A. (6) 86, 88 Ubasawa, M. (6) 88 Uchida, J. (1) 303 Uchida, Y. (1) 281; (3) 24 Uchiyama, M. (6) 41 Ueda, I. ( 7 ) 33 Ueda, K. (7) 139 Uehara, A. (1) 12 Uemura, M. (6) 79 Uenishi, J.-I. (7) 139 Ueyama, S. (8) 222 Ugi, I. (5) 90; (6) 3, 4 Uhlig, W. (1) 106; (8) 70 Uhlmann, E. (6) 97 Ullmann, J. (1) 257; (7) 11 Umezu, Y. (1) 80 Urdea, M.S. (6) 187, 188 Urogdi, L. (7) 64; (8) 47 Uskokvic, M.R. (3) 35 Usman, N. (4) 65; (6) 93 Usmanova, L.N. (1) 254; (4) 15, 91 Utley, J.H.P. (1) 280; (7) 2 Uziel, J. (5) 159 Uznanskl, B. (4) 67; (6) 108, 152, 153 Vacca, J.P. (5) 16, 17 Vahldiek, M. (1) 227 Vaidyanathaswamy, R. (5) 202 Valeeva, F.G. (5) 69 Valerio, R.M. (5) 29 Valero, R. (1) 271 van Asselt, R. (8) 20 van Boom, J.H. (4) 21, 44-46; (5) 168; (6) 46, 99

van de Grampel, J.C. (8) 178, 285, 290 van den Elst, H. (4) 21; (6) 99 van der Klein, P.A.M. (5) 168 van der Lee, A. (8) 290 van der Marel, G.A. (4) 21; (5) 168; (6) 46, 99 van der Plas, H.C. (5) 30, 31, 32 Van de Woerd, R. (6) 72 van Doorn, J.A. (1) 42, 76, 77, 191 van Genderen, M.H.P. (6) 238 van Malssen, K.F. (8) 20 van Oijen, A.H. (4) 46 Vanvalkenburgh, V. (1) 181 Van Wazer, J.R. (5) 73 Varghese, B. (8) 177 Varma, V. (8) 89 Varshney, A. (1) 37 Vasil'eva, N.V. (8) 253 Vaultier, M. (7) 13 Veale, C.A. (7) 96 Vedejs, E. (2) 19, 20; (3) 38; (7) 17, 18 Veits, Yu.A. (1) 349, 350; (8) 66 Velat-Bellini, A. (6) 65 Vemlshetti, P. (6) 19 Ven'yaminova, A.G. (6) 82, 143 Verfuerth, U. (6) 4 Verkade, J.G. (2) 46, 47; ( 5 ) 55 Vermes, B. (7) 115 Vesely, I. (1) 259 Veszpremi, T. (1) 439, 440

Vial, J.-M. (6) 84 Viaud, M.C. (1) 174 Victor, M.W. (8) 207, 208 Vidal, A. (5) 24; (7) 117, 118; (8) 52, 54, 56 Vidal, J.P. (1) 87; (7) 94 Vilaplana, M.J. (7) 121 Villa, R. (7) 60 VilliGras, J. (5) 108 Vinader, M.V. (1) 166; (7) 122, 127; (8) 62 Vincens, M. (1) 87 Vinogradova, S.V. (8) 212, 235, 252, 253 Visscher, J. (6) 72 Vogel, J. (2) 41 Vogt, H. (1) 145; (7) 37 Voigt, J.M. (6) 166

Voitsekhovskaya, O.M. (1) 1 Volkov, E.M. (6) 160 Volozhin, L.M. (1) 105 Vondung, J. (1) 327, 328 Vonk, C.R. (5) 30 Vonwiller, S.C. (3) 37 vo Quang, L. (7) 79 Vo Quang, Y. (7) 79 Vorbriiggen, H. (1) 148; ( 7 ) 51, 99 Vork, M.V. (8) 50 Voronkov, M.G. (1) 109 Vostrikov, N.S. (7) 98 Votava, V. (1) 259 Votruba, I. (6) 6 Vovelle, F. (6) 140 Vrieze, K. (8) 20 Vyas, D.M. (1) 171 Vyle, J.S. (4) 72, 73; (6) 155, 156 Vysotskii, V.I. (1) 97 Wada, H. (8) 264 Wada, M. (3) 22 Wagner, A. (1) 151, 153 Wagner, 0. (1) 379, 413, 457; (2) 34 Wakabayashi, H. (6) 50 Wakabayashl, S . (4) 41; (6) 39, 41, 42 Walker, B.J. (3) 23; ( 7 ) 29 Walker, D.M. ( 5 ) 171 Walker, P.A. (4) 59 Walker, R.T. ( 6 ) 10 Wallenhauer, S . (2) 7 Waltere, M.A. (5) 144 Walton, T.J. (6) 241 Wamhoff, H. (8) 77 Wang, D. (6) 89 Wang, G. (5) 156 Wmg, H.-E. (1) 34 Wang, J.S. (5) 50 Wang, L.Q. (5) 180 Wang, P. (2) 10 Wang, T. (7) 23, 27, 53; ( 8 ) 226 Wang, W.-D. (1) 209 Wang, Y. ( 6 ) 89 Wang, Y.Y. (6) 77 Wang, Z. (8) 111 Wangchareontrakul, S. (7) 134 Ward, W.J., jun. (2) 21; (7) 19 Warner, B.D. (6) 188 Warner, S . (1) 39 Warpehoski, M.A. (6) 232 Warren, S. (3) 28, 29 Wasiak, J. (5) 71

364

Wasielewski, C. (5) 167 Wasiucionek, M. (8) 258 Wasserman, H.H. (7) 106 Watabe, H. (8) 264 Watal, G. (6) 40 Watanabe, E. (8) 231 Watanabe, K. (6) 52 Watanabe, Y. (3) 38; (4) 42; (5) 19, 23 Watt, W. (6) 237 Watts, J . P . (7) 132 Webb, R.R. (5) 189 Webber, S.E. (7) 96 Weber, L. (1) 319-324, 373, 374 Weber, M. (1) 441 Weedon, B.C.L. (7) 88 Weferling, N. (1) 51-54, 86; (2) 27; (4) 29 Wei, L. (1) 39 Weichmann, H. (3) 21 Weidert, P . J . (1) 400; (5) 215 Weidner, C.H. (7) 101 Weidner, M.F. (6) 219 Weiler, L. (7) 111 Weinfield, M. (6) 147 Weiss, C.D. (1) 140; (5) 200; (8) 41 Weies, S. (6) 34 Weissman, S.A. (1) 414 Weker, M.F. (8) 99 Weller, D.D. (6) 133, 134 Weller, F . (1) 64 Welling, L.L. (1) 132 Wenzinger, G.R. (4) 37; (6) 116, 117 Wess, G . (3) 31 West, R. (1) 130 Westermann, H. (1) 310; (4) 86 Westman, E. (6) 126 Wetmur, J.G. (6) 118 Wettling, T. (1) 379 White, A.H. (1) 19 White, J . B . (7) 139 White, J.D. (7) 137 Whiteker, G.T. (1) 26 Whitesides, G.M. (6) 29 Whitlock, H.W. (3) 14 Whittaker, C. (7) 40 Whitten, J.E. (1) 37 Wiaterek, C. (1) 123, 124 Wicienski, N.A. (6) 232 Wickstrom, E. (4) 37; (6) 112, 116, 117 Widelav, A. (8) 9 Wieczorek, M.W. (3) 32, 44 Wieland, P. (1) 140 Wiemer, D.F. (5) 146, 147; (7) 141

Orgunophosphorus C 'hPmi s i n , Wierzorek, W. (3) 20 Wife, R.L. (1) 76 Wilde, R.L. (5) 220 Wilk, A. (4) 67; (6) 108, 153 Wilkinson, D.L. (1) 82, 158; (3) 4; (7) 5 Will, N. (1) 35; (5) 52 Willett, R.D. (5) 129 Williams, B.D. (6) 196 Williams, D . J . (7) 103 Williams, D.N. (8) 22 Williams, D.R. (7) 112 Williams, I . D . (1) 39 Williams, M. (5) 175 Williams, M.G. (6) 231 Williamson, M. (5) 78 Williard, P.G. (1) 68 Willingham, R.A. (8) 247, 248 Willis, A.C. (1) 104 Wilson, D.W. (6) 121 Wilusz, E . J . (5) 175 Wimmer, T. (1) 156 Winchester, W.R. (1) 68 Winfield, J.M. (1) 186 Winter, H. (8) 178 Wintergrass, D. (5) 55 Wippler, J . (6) 62 Wirkner, C. (1) 438 Wirth, U. (8) 24 Wisian-Neilson, P. (8) 224-230 Witt, M. (8) 1, 185, 186 Witzcak, M.K. (7) 3; (8) 10 Wojna-Tadeusiak, E. (5) 224 Wolf, R . (1) 403; (4) 85; (8) 8 Wolf, T. (6) 226 Wolfsberger, W. (1) 46, 47, 71, 163, 225; (8) 15, 17, 18 Wollenzien, P. (6) 203 Wolmershliuser, G. (1) 327, 328, 436 Won, Y.M. (8) 118, 161, 195 Wong, S.S. (6) 198 Wood, D.L. (7) 91 Woodward, P . R . (7) 103 Woolins, J.D. (8) 170 Woulfe, K.W. (1) 428 Wozniak, L. (5) 2, 223 Wright, M.E. (1) 7 Wright, W.W. (8) 271 wu, s.-Y. (5) 74 Wu, S.Y. (5) 47, 48 Wu, T. (6) 83 wu, X.P. (5) 180 Wulvik, E.A. (3) 25

Wurdeman, R.L. (6) 235 Wynne, K.J. (8) 215 Xi, S.K. .(2) 46, 47; (5) 55; (8) 26 Xiang, Y. (7) 52 Xie, X. (5) 150 Xu, J. (3) 3; (5) 109 xu, w. (1) 445 Xu, Y. (5) 164 Yadagiri, P. (5) 20 Yadau, V.K. (4) 5 Yagi, H. (6) 233 Yaguchi, A. (8) 122, 128, 134, 137, 138, 141, 142 Yagupol'skii, L.M. (2) 14 Yakigawa, Y. (8) 279 Yalovskaya, A.I. (1) 152 (7) 108 Yamada, €I. Yamagata, T. (1) 28 Yamagishi, T. (4) 80 Yamaguchi, H. (5) 196 Yamaguchi, K. (5) 59 Yamaguchi, M. (1) 80, 91; (4) 80; (5) 99; (7) 85 Yamekage, S. (6) 76, 79 Yamamoto, A. (1) 9 Yamamoto, H. (5) 118; (8) 267 Yamamoto, K. (8) 93, 94 Yamamoto, N. (4) 49, 50; (6) 55, 57 Yamamoto, S. (1) 267 Yamamoto, T. (8) 127, 162 Yamana, K. (4) 52, 53; (6) 54, 129 Yamanaka, H. (3) 40, 41 Yamane, H. (4) 49, 50; (6) 55, 57 Yamaahita, M. (3) 11; (5) 107 Yamaahita, T. (4) 92 Yamashita, Y. (7) 80; (8) 276278 Yamataka, H. (7) 20 Yamazoes, 0. (8) 168 Yamoto, s. (4) 53 Yanagi, K. (1) 9 Yankovskapa, V.L. (5) 37 Yanovekii, A.I. (1) 263 Yasnikova, N.A. (1) 143 Yasuda, M. (4) 92 Yasuhiro, Y. (8) 162 Yau, E.K. (4) 70; (6) 122, 125 Yazawa, N. (1) 298 Yeh, H.J.C. (6) 233

Author Index Yeh, J.T. (1) 118 Yeung, A.S. (8) 87 Yeung Lam KO, Y.Y.C.

365 Yurchenko, A.G. (1)

361, 367

Yieh, C.-H. (1) 33 Yonaga, M. (7) 139 Yoneda, A. (5) 196 Yoneda, R. (5) 85-87 Yonekura, K. (1) .267 Yonetake, K. (8) 233 Yoon, H.S. (8) 161 Yoehlda, Y. (1) 298, 299 Yoshlfujl, M. (1) 311, 314, 357, 358 Yoehlkawa, Y. (8) 154, 222 Yoehlnari, It. (5) 68 Young, K.H. (8) 174 Young, S.G. (8) 199, 200, 246 Youelf, N.M. (2) 25; (5) 182 Yozhuehko, B.N. (5) 95 Yuan, C. (2) 12; (5) 63, 112, 150, 156, 164, 211-213 Yuan, Q. (5) 150

(1) 1;

(8) 12

Yurchenko, R . I .

(1) 1;

(8) 12

Yvergnaux, F. (7) 113, 114

Zabarylo, S. (4) 57 Zablocka, M. (3) 20, 44, 45

Zaikov, G.E. (8) 164 Zaln, R. (6) 126 Zaltaeva, G.V. (6) 9 Zak, B. (1) 259 zakharov, L.S. (5) 10-12, 60 Zalaehko, L.M. (6) 5 Z a l w e k l , D.J. (1) 177 Zal'taPan, I.S. (2) 49; (8) 40, 67 Zamal,

H. (6) 65

Zamecnik, P.C. (6) 120 Zanin, B. (8) 106, 107 Z a r l l n g , D.A. (6) 176 Z a r m , D. (1) 194 Zawada, E. (1) 207

Zecchi, G. (8) 51 Z e l l n e r , K. (1) 69 Zemlyanoi, V.N. (1) 98 Z e n j i , N. (8) 201 Zenkova, M.A. (6) 82 Zenneck, V. (1) 380 Zhang, J.-L. (1) 445 Zhao, Y. (5) 46 Zhou, X.-X. (6) 84 Zhu, J. (3) 3; (5) 109 Zhut-skli, P.V. (4) 4 Ziehlermartln, J.P. (4) 59

Zielonacka-Lie, Zlmnerman, S.C. Zimmcfaann, fi. Zlnchenko, A.I. Zlnovich, Z.Z.

E. (6) 8

(6) 236 (8) 24 (6) 5 (8) 216 Zon, G. (6) 101, 102, 108, 113, 121 Zorln, B.Ya. (5) 133 Zoeolapova, Z.A. (6) 143 Zsolnal, L. (1) 406, 407 Zurmeuhlen, F. (1) 398 Zyablikova, T.A. (1) 265; (5) 121, 183, 198 Zykova, T.V. (1) 233, 234