Sulphinic Acids, Esters and Derivatives (1990)

731 Pages·1990·22.85 MB·English

The chemistry of
sulphinic acids, esters
and their derivatives
THE CHEMISTRY OF FUNCTIONAL GROUPS
A series of advanced treatises under the yeneral editorship of
Professor Saul Putui
The chemistry of alkenes (2 volumes)
The chemistry of the carbonyl group (2 volumes)
The chemistry of the ether linkage
The chemistry of the amino yroup
The chemistry of the 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 cyano 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 imidates
The chemistry of cyanates and their thio derivatives (2 parts)
The chemistry of diazonium and diazo groups (2 parts)
The chemistry of the carbon-carbon triple bond (2 parts)
The chemistry of ketenes allenes and related compounds (2 parts)
The chemistry of the sulphonium group (2 parts)
Supplement A The chemistry of double bonded functional groups (2 volumes 4 parts)
Supplement B The chemistry of acid derivatives (2 parts)
Supplement C The chemistry of triple-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 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 tellurium compounds (2 volumes)
The chemistry of the cyclopropyl group
The chemistry of sulphones and sulphoxides
The chemistry of organic silicon compounds (2 parts)
The chemistry of enones (2 parts)
UPDATES
The chemistry of z haloketones z haloaldehydes
and u-haloimines
Nitrones nitronates and nitroxides
Crown ethers and analogs
R0
-S.
‘OH
The chemistry of
sulphinic acids, esters and
their derivatives
Edited by
SAUL PATAI
The Hebrew University, Jerusalem
1990
JOHN WILEY & SONS
CHICHESTER - NEW YORK - BRISBANE - TORONTO - SINGAPORE
An Interscience" Publication
Copyright 0 1990 by John Wiley & Sons Ltd
Baffns Lane, Chichester, West Sussex POlY 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 OfJices
John Wiley & Sons, Inc., 605 Third Avenue,
New York, NY 10158-0012, USA
Jacaranda Wiley Ltd, G.P.O. Box 859, Brisbane,
Queensland 4001, Australia
John Wiley & Sons (Canada) Ltd, 22 Worcester Road,
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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 Cat~ogjn~-~-PubticatjDoant a:
The Chemistry of sulphinic acids, esters and their derivatives /
edited by Saul Patai.
p. cm.-(The Chemistry of functional groups)
‘An Interscience publication.’
Bibliography: p.
Includes index.
ISBNO 471 91918 7
1. Sulphinic acids. 2. Esters. 1. Patai, Saul. 11. Series.
QD341.A2C4175 1990 89-31592
546.72322-dc20 CIP
British Library Cataloguing in Publication Data:
Patai, Saul
The chemistry of sulphinic acids, esters and their
derivatives.
1. Organic sulphur compounds
I. Title 11. Series
547.06
ISBNO 471 91918 7
Typeset by Thomson Press (India) Ltd, New Delhi, India.
Printed in Great Britain by Courier International Ltd, Tiptree, Essex
Contributing authors
M. R. F. Ashworth Organische und Instrumentelle Analytik, Universitat des
Saarlandes, D-6600 Saarbrucken, FRG
H. Basch Department of Chemistry, Bar Ilan University, Ramat
Gan 52100, Israel
A. Bassindale POCRG, Department of Chemistry, The Open Univers-
ity, Walton Hall, Milton Keynes, MK7 6AA, UK
S. Braverman Department of Chemistry, Bar-Ilan University, Ramat-
Gan 59100, Israel
B. Bujnicki Centre of Molecular and Macromolecular Studies, Polish
Academy of Sciences, Department of Organic Sulphur
Compounds, Sienkiewicza 1 12, 90-363 Xbdi, Poland
G. Capozzi Department of Organic Chemistry, University of Firenze,
Via G. Carponi 9, 50121 Firenze, Italy
D. C. Dittmer Department of Chemistry, Syracuse University, Syracuse,
NY 13244-1200, USA
J. Drabowicz Centre of Molecular and Macromolecular Studies, Polish
Academy of Sciences, Department of Organic Sulphur
Compounds, Sienkiewicza 112, 90-363 Xbdi, Poland
T. Endo Research Laboratory of Resources Utilization, Tokyo
Institute of Technology, Nagatsuta-cho, Midori-ku,
Yokohama 227, Japan
H. Fujihara Department of Chemistry, The University of Tsukuba,
Tsukuba, Ibaraki 305, Japan
N. Furukawa Department of Chemistry, The University of Tsukuba,
Tsukuba, Ibaraki 305, Japan
M. D. Hoey Department of Chemistry, Syracuse University, Syracuse,
NY 13244-12 00, USA
V
vi Contributing authors
J. Hoyle Chemistry-Soils Department, Nova Scotia Agricul-
tural College, P.O. Box 550, Truro, Nova Scotia B2N 5E3,
Canada
J. Hey POCRG, Department of Chemistry, The Open Univer-
sity, Walton Hall, Milton Keynes, MK7 6AA, UK
A. Kalir Department of Physiology and Pharmacology, Sackler
Faculty of Medicine, Tel Aviv University, Tel Aviv 69978,
Israel
H. H. Kalir Department of Neurobiology, Mount Sinai School of
Medicine, One Gustave L. Levy Place, New York,
NY 10029. USA
P. Kielbasinski Centre of Molecular and Macromolecular Studies, Polish
Academy of Sciences, Department of Organic Sulphur
Compounds, Sienkiewicza 1 12, 90-363 Xbdz, Poland
M. M. Mikolalczyk Centre of Molecular and Macromolecular Studies, Polish
Academy of Sciences, Department of Organic Sulphur
Compounds, Sienkiewicza 112,363 Xbdz, Poland
A. Nudelman Department of Chemistry, Bar Ilan University, Ramat
Gan 51 100, Israel
S. Oae Department of Chemistry, Okayama University of
Science, Ridai-cho 1-1, Okayama 700, Japan
T. Okuyama Department of Chemistry, Faculty of Engineering
Science, Osaka University, Toyonaka, Osaka 560, Japan
J. Omelariczuk Centre of Molecular and Macromolecular Studies, Polish
Academy of Sciences, Department of Organic Sulphur
Compounds, Sienkiewicza 112, 90-363 KOdi, Poland
K. Pihlaja Department of Chemistry, University of Turku, SF-20500
Turku, Finland
P. Sarti-Fantoni Department of Organic Chemistry, University of Firenze,
Via G. Carponi 9, 50121 Firenze, Italy
J. Shorter Department of Chemistry, The University, Hull, HU6
7RX, UK
C. J. M. Stirling Department of Chemistry, University College of North
Wales, Bangor, Gwynedd LL7 2UW, UK
T. Takata Research Laboratory of Resources Utilization, Tokyo
Institute of Technology, 4259 Nagatsuta-cho, Midori-ku,
Yokohama 227, Japan
Contributing authors vii
J. G. Tillett Department of Chemistry and Biological Chemistry,
University of Essex, Wivenhoe Park, Colchester, C04
3SQ, UK
H. Togo Department of Chemistry, Faculty of Science, Chiba
University, Yayoi-cho, Chiba City, 260 Japan
U Zoller Division of Chemical Studies, Haifa University, School
of Education, Oranim, Kiryat Tivon 36910, Israel
Foreword
This volume on sulphinic acids and their derivatives belongs to a subset on sulphur-
containing functional groups within the framework of The Chemistry of Functional
Groups. The first ofthis subset was The Chemistry ofthe 7hiol Group(two parts, 1974), with
much additional material on the subject published in Supplement E: The Chemistry of
Ethers, Crown Ethers, Hydroxyl Groups and their Sulphur Analogues (two parts, 1980). A
volume on The Chemistry ofthe Sulphonium Group appeared in two parts in 1981 and a
volume on The Chemistry ofSulphones and Sulphoxides in 1988. The present volume deals
with sulphinic acids and their esters, halides and amides. A volume on sulphenic acids is
already in the proof stage and is scheduled to appear in the late spring of 1990, and
manuscripts for a volume on sulphonic acids are reaching the editors now, and will be
published, we hope, in early 1991.
Among the chapters originally planned for the present volume, three did not
materialize. These are on structural chemistry, on electrochemistry and on free radical
chemistry. We hope to include these subjects in a supplementary volume on the whole
subset of sulphur-containing functional groups, to be published in a few years’ time.
The references in almost all chapters cover the year 1987 and in many cases extend well
into 1988.
I would like to thank my good friends, Professor C. J. M. Stirling FRS and Professor Zvi
Rappoport, for their generous and unstinting advice and counsel during the preparation of
the plan of the present volume.
I will be grateful to readers who would call my attention to omissions and mistakes in
this volume.
Jerusalem SAUI. PATAI
October 1989
ix
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 or 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, photochemis-
xi
xii Preface to the series
try, radiation chemistry, thermochemistry, syntheses and uses of isotopically labelled
compounds, as well as with biochemistry, pharmacology and toxicology. Whenever
applicable, unique chapters relevant only to single functional groups are also included (e.g.
‘Poly ethers’, ‘Tetraaminoethylenes’ or ‘Siloxanes’).
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 pateint 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 PATAI
Jerusalem Israel