Sulphur-Containing Functional Groups (1993)

1125 Pages·1993·24.023 MB·English

Supplement S
The chemistry of
sulphur-containing functional groups
THE CHEMISTRY OF FUNCTIONAL GROUPS
A series of advanced treatises under the general editorship of
Professor Saul Patai
The chemistry of alkenes (2 volumes)
The chemislry of Ihe carbonyl group (2 volumes)
The chemislry of the ether linkage
The chemistry of the amino group
The chemislry of nitro and nitroso groups (2 parts)
The chemistry of carboxylic acids and esters
The chemistry of the carbon-nitrogen double bond
The chemistry of amides
The chemistry of the cyan0 group
The chemistry of the hydroxyl group (2 parts)
The chemistry of the azido group
The chemistry of acyl halides
The chemistry of the carbon-halogen bond (2 parts)
The chemistry of the quinonoid compounds (2 volumes, 4 parts)
The chemistry of the thiol group (2 parts)
The chemistry of the hydrazo. azo and azoxy groups (2 parts)
The chemistry of amidines and imidales (2 volumes)
The chemistry of cyanates and their thio derivatives (2 parts)
The chemislry of diazonium and diazo groups (2 parts)
The chemistry of the carbon-carbon triple bond (2 parls)
The chemistry of ketenes. allenes and related compounds (2 parts)
The chemistry of the sulphonium group (2 parls)
Supplemenl A: The chemistry of double-bonded functional groups (2 volumes, 4 parts)
Supplement B: The chemistry of acid derivatives (2 volumes, 4 parts)
Supplement C: The chemistry of Iriple-bonded functional groups (2 parts)
Supplement D: The chemistry of halides, pseudo-halides and azides (2 parts)
Supplement E: The chemistry of ethers, crown ethers. hydroxyl groups
and their sulphur analogues (2 volumes, 3 parts)
Supplement F: The chemistry of amino, nitroso and nitro compounds
and their derivatives (2 parts)
The chemistry of the metal-carbon bond (5 volumes)
The chemistry of peroxides
The chemistry of organic selenium and lellurium compounds (2 volumes)
The chemistry of the cyclopropyl group (2 parts)
The chemistry of sulphones and sulphoxides
The chemistry of organic silicon compounds (2 parts)
The chemistry of enones (2 parts)
The chemistry of sulphinic acids, esters and their derivatives
The chemistry of sulphenic acids and their derivatives
The chemistry of enols
The chemistry of organophosphorus compounds (2 volumes)
The chemistry of sulphonic acids, esters and their derivatives
The chemistry of alkanes and cycloalkanes
Supplement S: The chemistry of sulphur-containing lunclional groups
UPDATES
The chemistry of a-haloketones. a-haloaldehydes and a-haloimines
Nitrones. nitronates and nitroxides
Crown ethers and analogs
Cyclopropane derived reactive intermediates
Synlhesis of carboxylic acids, esters and their derivatives
The silicon-heteroatom bond
Synthesis of lactones and laclams
Palai's 1992 guide to the chemistry of functional groups-Saul Patai
Supplement S
The chemistry of
sulphur-containing functional
groups
Edited by
SAULP ATAI
and
ZVIR APPOPORT
The Hebrew University, Jerusalem
1993
JOHN WILEY & SONS
CHICHESTER-NEW YORK-BRISBANE-TORONTO-SINGAPORE
An Interscience@P ublication
Copyright 0 1993 by John Wiley & Sons Ltd,
Bafins Lane, Chichester,
West Sussex PO19 IUD, England
All rights reserved.
No part of this book may be reproduced by any means,
or transmitted, or translated into a machine language
without the written permission of the publisher.
Other Wiley Editorial Offices
John Wiley & Sons, Inc., 605 Third Avenue,
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Queensland 4001, Australia
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John Wiley & Sons (SEA) Pte Ltd, 37 Jalan Pemimpin #05-04,
Block B, Union Industrial Building, Singapore 2057
Library of Congress Cataloging-in-P ublication Data
The Chemistry of sulphur-containing functional groups / edited by Saul
Patai and Zvi Rappoport.
p. cm.-(Chemistry of functional groups. Supplement ; S)
‘An Interscience publication.’
Includes bibliographical references and index.
ISBN 0 471 93046 6
1. Organosulfur compounds. I. Patai, Saul. 11. Rappoport, Zvi.
111. Series.
QD305. S3C48 1993
541’. 06-dc20 92-23016
CIP
British Library Cataloguing in Publication Data
A catalogue record for this book is available from the British Library
ISBN 0 471 93046 6
Typeset by Thomson PreFs (India) Ltd, New Delhi, India
Printed and bound in Great Britain by Biddles Ltd, Guildford, Surrey
Contributing authors
Harold Basch Department of Chemistry, Bar-Ilan University, Ramat-
Gan 52900, Israel
Alan R. Bassindale Department of Chemistry, The Open University, Walton
Hall, Milton Keynes, MK7 6AA, UK
Gernot Boche Fachbereich Chemie, Philipps-Universitat Marburg,
Hans Meerwein Strasse, D-3550 Marburg, Germany
C. Chatgilialoglu Istituto dei Composti del Carbonio Contenenti Etero-
atomi e loro Applicazioni, Consiglio Nazionale delle
Richerche, Via della Chimica 8, 1-40064 Ozzano Emilia
(Bologna), Italy
Jerzy Cioslowski Department of Chemistry, The Florida State University,
Tallahassee, Florida 32306-3006, USA
Kristine S. K. Crawford Department of Chemistry and Biochemistry, University
of Maryland, Baltimore County Campus, 5401 Wilkens
Ave., Baltimore, Maryland 21 228-5398, USA
J6sef Drabowicz Department of Organic Sulfur Compounds, Centre of
Molecular and Macromolecular Studies, Polish Academy
of Sciences, 90-363 todi, Sienkiewicza 112, Poland
M. Guerra lstituto dei Composti del Carbonio Contenenti Etero-
atomi e loro Applicazioni, Consiglio Nazionale delle
Richerche, Via della Chimica 8, 1-40064 Ozzano Emilia
(Bologna), Italy
Tova Hoz Department of Chemistry, Bar-Ilan University, Ramat
Can 52900, Israel
James N. lley Department of Chemistry, The Open University, Walton
Hall, Milton Keynes, MK7 6AA, UK
Steen lngemann Institute of Mass Spectrometry, University of Amsterdam,
Nieuwe Achtergracht 129, 1018 WS Amsterdam, The
Netherlands
Asher Kalir Department of Physiology and Pharmacology, Sackler
Faculty of Medicine, Tel Aviv University, Tel Aviv 69978,
Israel
Henry H. Kalir Department of Neurobiology, Mount Sinai School of
Medicine, One Gustave L. Levy Place, New York, NY
10029, USA
Marianna Kanska Department of Chemistry, University of Warsaw,
Warsaw, Poland
Wolfram Koch lnstitut fur Organische Chemie, Technische Universitat
Berlin, Strasse des 17 Juni 135, D-1000 Berlin 12,
Germany
V
vi Contributing authors
Leo J. de Koning Institute of Mass Spectrometry, University of Amsterdam,
Nieuwe Achtergracht 129, 1018 WS Amsterdam, The
Netherlands
Eitan €3. Krein Department of Organic Chemistry, The Hebrew
University of Jerusalem, Jerusalem 9 1904, Israel
Joel F. Liebman Department of Chemistry and Biochemistry, University
of Maryland, Baltimore County Campus, 5401 Wilkens
Ave., Baltimore, Maryland 21228-5398, USA
John C. W. Lohrenz Fachbereich Chemie, Philipps-Universitat Marburg,
Hans Meerwein Strasse, D-3550 Marburg, Germany
Piotr ty iwa Department of Organic Sulfur Compounds, Centre of
Molecular and Macromolecular Studies, Polish Academy
of Sciences, 90-363 Lodz, Sienkiewicza 112, Poland
Gonzalo Martin Instituto Venezolano de Investigaciones Cientificas
(IVIC), Apartado 21 827, Caracas 1020A, Venezuela
Marian Mikdajczyk Department of Organic Sulfur Compounds, Centre of
Molecular and Macromolecular Studies, Polish Academy
of Sciences, 90-363 Zodz, Sienkiewicza 1 12, Poland
Nico M. M. Nibbering Institute of Mass Spectrometry, University of Amsterdam,
Nieuwe Achtergracht 129, 1018 WS Amsterdam, The
Netherlands
F. G. Riddell Department of Chemistry, The University of St Andrews,
St Andrews, KY16 9ST, Scotland, UK
BBla Rozsondai Structural Chemistry Research Group, Hungarian
Academy of Sciences, Eotvos University, P.O. Box 117,
H-1431 Budapest, Hungary
D. P. N. Satchell Department of Chemistry, King’s College London,
Strand, London WC2R 2LS, UK
R. S. Satchell Department of Chemistry, King’s College London,
Strand, London WCZR 2LS, UK
Bagrat A. Shainyan Irkutsk Institute of Organic Chemistry, Siberian Branch
of the Russian Academy of Sciences, 664033 Irkutsk,
Russia
Jacques Simonet Laboratoire Electrochemie, Universite de Rennes I,
d‘
Campus de Beaulieu, Avenue du Gknkral Leclerc, 35042
Rennes Cedex, France
Rajeeva Singh ImmunoGen, Inc., 148 Sidney Street, Cambridge,
Massachusetts 02139, USA
Suzanne W. Slayden Department of Chemistry, George Mason University,
4400 University Drive, Fairfax, Virginia 22030-4444,
USA
Boris A. Trofimov Irkutsk Institute of Organic Chemistry, Siberian Branch
of the Russian Academy of Sciences, 664033 Irkutsk,
Russia
George M. Whitesides Department of Chemistry, Harvard University, 12
Oxford Street, Cambridge, Massachusetts 021 38, USA
Mieczyslaw Zielihski Isotope Laboratory, Faculty of Chemistry, Jagiellonian
University, Cracow, Poland
The series The Chemistry of Functional Groups contains seven volumes of a sub-series
concerning sulphur containing functional groups, published between 1974 and 1991.
These volumes were the following:
The chemistry of the thiol group (1974)
Supplement E. The chemistry of ethers, crown ethers, hydroxyl groups and their
sulphur analogues (1980)
The chemistry of the sulphonium group (1981)
The chemistry of sulphones and sulphoxides (1988)
The chemistry of sulphinic acids, esters and their derivatives (1990)
The chemistry of sulphenic acids and their derivatives (1990)
The chemistry of sulphonic acids, esters and their derivatives (1991)
Many subjects dealt with in the chapters contained in the above volumes have
developed considerably since their publication and we felt that they should be updated.
In addition we were interested in publishing some chapters which did not materialize
for the original volumes, as well as some chapters which were on completely new subjects.
This was the motivation for offering the present supplementary volume to our readers.
Inevitably, not all the planned chapters materialized. Among these were chapters on
the following subjects: ‘Sulphur containing free radicals in photochemical processes’,
‘Sulphonates as nucleophiles’, ‘Sulphur containing ylides’, and finally and most
regrettably, ‘Safety, toxicity and environmental effects’.
The authors’ literature search in most cases extended up to the Spring of 1992.
We will be indebted to readers who will bring to our attention mistakes or omissions
in this or in any other volume of The Chemistry of Functional Groups series.
Jerusalem SAULP ATAI
June 1993 Zvr RAPPOPORT
vii
The Chemistry of Functional Groups
Preface to the series
The series ‘The Chemistry of Functional Groups’ was originally planned to cover in
each volume all aspects of the chemistry of one of the important functional groups in
organic chemistry. The emphasis is laid on the preparation, properties and reactions of
the functional group treated and on the effects which it exerts both in the immediate
vicinity of the group in question and in the whole molecule.
A voluntary restriction on the treatment of the various functional groups in these
volumes is that material included in easily and generally available secondary or tertiary
sources, such as Chemical Reviews, Quarterly Reviews, Organic Reactions, various
‘Advances’ and ‘Progress’ series and in textbooks (i.e. in books which are usually found
in the chemical libraries of most universities and research institutes), should not, as a
rule, be repeated in detail, unless it is necessary for the balanced treatment of the
topic. Therefore each of the authors is asked not to give an encyclopaedic coverage of
his subject, but to concentrate on the most important recent developments and mainly
on material that has not been adequately covered by reviews or other secondary sources
by the time of writing of the chapter, and to address himself to a reader who is assumed
to be at a fairly advanced postgraduate level.
It is realized that no plan can be devised for a volume that would give a complete
coverage of the field with no overlap between chapters, while at the same time preserving
the readability of the text. The Editor set himself the goal of attaining reasonable
coverage with moderate overlap, with a minimum of cross-references between the
chapters. In this manner, sufficient freedom is given to the authors to produce readable
quasi-monographic chapters.
The general plan of each volume includes the following main sections:
(a) An introductory chapter deals with the general and theoretical aspects of the group.
(b) Chapters discuss the characterization and characteristics of the functional groups,
i.e. qualitative and quantitative methods of determination including chemical and
physical methods, MS, UV, IR, NMR, ESR, and PES-as well as activating and directive
effects exerted by the group, and its basicity, acidity and complex-forming ability.
(c) One or more chapters deal with the formation of the functional group in question,
either from other groups already present in the molecule or by introducing the new
group directly or indirectly. This is usually followed by a description of the synthetic
uses of the group, including its reactions, transformations and rearrangements.
(d) Additional chapters deal with special topics such as electrochemistry, photo-
chemistry, radiation chemistry, thermochemistry, syntheses and uses of isotopically
labelled compounds, as well as with biochemistry, pharmacology and toxicology. When-
ever applicable, unique chapters relevant only to single functional groups are also
included (e.g. ‘Pol yethers’. ‘Tetraaminoethylenes’ or ‘Siloxanes’).
ix
X Preface to the series
This plan entails that the breadth, depth and thought-provoking nature of each chapter
will differ with the views and inclinations of the authors and the presentation will
necessarily be somewhat uneven. Moreover, a serious problem is caused by authors who
deliver their manuscript late or not at all. In order to overcome this problem at least
to some extent, some volumes may be published without giving consideration to the
originally planned logical order of the chapters.
Since the beginning of the Series in 1964, two main developments occurred. The first
of these is the publication of supplementary volumes which contain material relating to
several kindred functional groups (Supplements A, B, C, D, E and F). The second
ramification is the publication of a series of 'Updates', which contain in each volume
selected and related chapters, reprinted in the original form in which they were published,
together with an extensive updating of the subjects, if possible, by the authors of the
original chapters. A complete list of all above mentioned volumes published to date will
be found on the page opposite the inner title page of this book.
Advice or criticism regarding the plan and execution of this series will be welcomed
by the Editor.
The publication of this series would never have been started, let alone continued,
without the support of many persons in Israel and overseas, including colleagues, friends
and family. The efficient and patient co-operation of staff members of the publisher also
rendered me invaluable aid. My sincere thanks are due to all of them, especially to
Professor Zvi Rappoport who, for many years, shares the work and responsibility of
the editing of this Series.
The Hebrew University SAUL PATAl
Jerusalem, Israel
Contents
1. General and theoretical 1
Tova Hoz and Harold Basch
2. Structural chemistry of organosulfur compounds 101
Bela Rozsondai
3. The conformational analysis of sulphur-containing rings 175
F. G. Riddell
4. Thermochemistry of organosulphur compounds 197
Joel F. Liebman, Kristine S. K. Crawford and Suzanne W. Slayden
5. NMR and ESR of organosulphur compounds 245
Alan R. Bassindale and James N. lley
6. Mass spectra of organosulfur compounds 293
Nico M. M. Nibbering, Steen Ingemann and Leo J. de Koning
7. Carbon acidity resulting from sulfur substituents 339
Gernot Boche, John C. W. Lohrenz, Jerzy Cioslowski and
Wolfram Koch
8. Thiyl radicals 363
C. Chatgilialoglu and M. Guerra
9. Pyrolysis of organosulphur compounds 395
Gonzalo Martin
10. Electrochemical behavior of organic molecules containing sulfur 439
Jacques Simonet
11. Syntheses and uses of isotopically labelled compounds with sulphur-
containing functional groups 495
Mieczydaw Zielinski and Marianna Kanska
12. Soft metal ion-promoted reactions of organo-sulphur compounds 599
D. P. N. Satchell and R. S. Satchell
13. Thiol-disulphide interchange 633
Rajeeva Singh and George M. Whitesides
14. Vinyl sulfides 659
Boris A. Trofimov and Bagrat A. Shainyan
15. High-coordinated sulfur compounds 799
Jozef Drabowicz, Piotr Zyzwa and Marian Mikolajczyk
xi