ORGANIC REACTION MECHANISMS * 1991

Transcription

1 ORGANIC REACTION MECHANISMS * 1991

2 ORGANIC REACTION MECHANISMS 1991 An annual survey covering the literature duted December 1990 to November 1991 Edited by A. C. Knipe and W. E. Watts University of Ulster Northern Ireland An Interscience" Publication JOHN WILEY & SONS Chichester. New York. Brisbane * Toronto. Singapore

3 Copyright 1993 by John Wiley & Sons Ltd, Raffins Lane, Chichester, West Sussex PO19 IUD, England All rights reserved No part of rhe book may be reproduced by any means, or transmitted, or translated into a machine language without [hc written permission of the publisher. Other Wiley Edimriul 0fice.s John Wiley & Sons, Inc., 605 Third Avenue, New York, NY 1015R (JSA Jacaranda Wiley Ltd, G.P.O. Box 859. Brisbane. Queensland 4001, Australia John Wiley & Sons (Canada) Ltd, 22 Worcester Road, Rexdale, Ontario M9W Canada John Wlley & Sons (SEA) Pte Ltd, 37 Jalan Pemimpin #05-04, Block B, Union Industrial Building, Singapore 2057 library of Congress Catalog Card Number Britkh Lihravy Cataloguing in Publication Data: Organic reaction mechanisms 1. Organic compounds. Chemical reactions Mechanisms-Serials Y ISBN Typeset by Techset Cornposition Ltd, Salisbury. UK. Printed and hound in Great Britain by Biddles Ltd. Giiildford, Surrey

4 Contributors R. A. AITKEN W. R. BOWMAN R. C. COOMBES M. R. CRAMPTON N. DENNIS G. W. J. FLEET A. C. KNIPE P. KOCOVSKY H. MASKILL A. W. MURRAY M. I. PAGE C. J. RHODES J. SHORTER W. J. SPILLANE A. THIBBLIN Department of Chemistry, University of St Andrews, Fife KY16 9ST, UK Department of Chemistry, Loughborough University, Leicester, UK Department of Chemistry, Brunel, University of West London, Uxbridge, Middlesex UB8 3PH, UK Department of Chemistry, Durham University, Durham DH1 3LE, UK Australian Commercial Research and Development Ltd, GPO Box 2481, Brisbane, Queensland 4001, Australia Dyson Perrins Laboratory, Oxford University, South Parks Road, Oxford OX1 3QT, UK Department of Applied Physical Sciences, University of Ulster, Coleraine, Co Londonderry BT52 lsa, UK Department of Chemistry, University of Leicester, Leicester LEI 7RH, UK Department of Chemistry, University of Newcastle upon Tyne, Newcastle upon Tyne NEl 7RU, UK Department of Chemistry, University of Dundee, Dundee DD1 4HN, UK Department of Chemical Sciences, University of Huddersfield, Queensgate, Huddersfield, W Yorkshire, UK Department of Chemistry, Queen Mary and Westfield College, University of London, Mile End Road, London El 4NS, UK School of Chemistry, University of Hull, Hull HU6 7RX, UK Department of Chemistry, University College, Galway, Ireland Institute of Chemistry, University of Uppsala, P.O. Box 531, S Uppsala, Sweden V

5 Preface The present volume, the twenty-seventh in the series, surveys research on organic reaction mechanisms described in the literature dated December 1990 to November In order to limit the size of the volume, we must necessarily exclude or restrict overlap with other publications which review specialist areas (e.g. photochemical reactions, biosynthesis, electrochemistry, organometallic chemistry, surface chemistry and heterogeneous catalysis). In order to minimize duplication, while ensuring a comprehensive coverage, the editors conduct a survey of all relevant literature and allocate publications to appropriate chapters. While a particular reference may be allocated to more than one chapter, we do assume that readers will be aware of the alternative chapters to which a borderline topic of interest may have been preferentially assigned. There have been two changes of author since last year and we welcome Dr W. R. Bowman (Loughborough University) and Dr H. Maskill (University of Newcastle upon Tyne) who have contributed reviews of Radical Reactions and Carbocations, respectively. They replace Dr P. Hanson and Dr R. A. Cox whose expert contributions to this continuing series are gratefully acknowledged. Once again we wish to thank the publication and production staff of John Wiley & Sons and our team of experienced contributors for their efforts to ensure that the standards of this series are sustained. We are also indebted to Dr N. Cully, who complied the subject index. A.C.K. W.E.W. vii

6 Contents Reactions of Aldehydes and Ketones by M. I. Page Reaction of Acids and their Derivatives by W. J. Spillane Radical Reactions: Part 1 by W. R. Bowman Radical Reactions: Part 2 by C. J. Rhodes Oxidation and Reduction by G. W. J. Fleet Carbenes and Nitrenes by R. A. Aitken Nucleophilic Aromatic Substitution by M. R. Crampton Electrophilic Aromatic Substitution by R. G. Coombes Carbocations by H. Maskill Nucleophilic Aliphatic Substitution by J. Shorter Carbanions and Electrophilic Aliphatic Substitution by A. C. Knipe Elimination Reactions by A. Thibblin Addition Reactions: Polar Addition by P. KoEovsky Addition Reactions: Cycloaddition by N. Dennis Molecular Rearrangements by A. W. Murray Author Index, Subject Index, ix