Heterocyclic Chemistry Volume 4 A Specialist Periodical Report Heterocyclic Chemistry Volume 4 A Review of the Literature Abstracted between July 1981 and June 1982 Senior Reporters H. Suschitzky Department of Chemistry and Applied Chemistry, University of Salford 0 . Meth-Cohn C.S./.R.,Pretoria, South Africa Reporters G . V. Boyd Chelsea College, London S . D. Carter Queen Elizabeth College, London G . W. H . Cheeseman Queen Elizabeth College, London G . P. Ellis UWIST, Cardiff S. Gronowitz University of Lund, Sweden 0 . Guilloton University of Nantes, France T. V. Lee Brunel University, Middlesex J. R. Malpass University of Leicester T. J. Mason Lanchester Polytechnic, Coventry H. Quiniou University of Nantes, France J. M. E. Quirke Florida International University, USA J. T. Sharp University of Edinburgh The Royal Society of Chemistry Burlington House, London W I V OBN ISBN 0-85 186-833-9 ISSN 0144-8773 Copyright 0 1985 The Royal Society of Chemistry All Rights Reserved No part of this book may be reproduced or transmitted in any form or by any means - graphic, electronic, including photocopying, recording, taping, or information storage and retrieval systems - without written permission from The Royal Society of Chemistry Printed in Great Britain at the Alden Press, Oxford, London and Northampton In tr oduc t ion Volume 4 includes the abstracted literature on heterocyclic chemistry between July 1981 and June 1982 (i.e. Volumes 95 and 96 of Chemical Abstracts). The format of previous volumes in respect of chapter arrangement has been retained, to allow the reader to study readily the progress in an area of heterocyclic chemistry through all of the four volumes, helped also by a detailed list of Contents. Our reviewers have again admirably succeeded in distilling out the salient features of several thousand references and have presented them in a concise and readable report. They have also co-operated with skill and patience in a cost-cutting exercise designed by the RSC editors, and have produced diagrams by a new method. I t is hoped that these efforts will ensure the economic survival of the series and eventually bring down the price to a level which will tempt the individual buyer; the only serious and recurring printing mistake, as one illustrious heterocyclic chemist remarked, is the price! Our thanks to all authors for their forbearance in the handling of gridsheets and supplying excellent manuscripts, and to the editorial staff of the Royal Society of Chemistry for smoothing out difficulties. H. Suschitzky and 0. Meth-Cohn Contents Chapter 1 Three-Membered Ring Systems By T. J. Mason 1 1 Reviews General Rings containing Oxygen Rings containing Nitrogen Rings containing Sulphur 1 1 2 Oxirans Preparation Oxidation of Alkenes, using Oxygen or Oxygencontaining Gases Oxidation of Alkenes by Peroxy-acids Oxidation of Alkenes, using Peroxides Synthesis by Halohydrin Cyclizations and Related Reactions Synthesis via Attack of a Carbanion on the Carbonyl Group of Aldehydes and Ketones Synthesis of Chiral Oxirans Synthesis and Reactivities of Aromatic Oxides Miscellaneous Syntheses Spectra and Theoretical Chemistry Reactions Ring-opening Reactions with Electrophiles Cyclization Reactions N ucleophilic Ring-opening Reactions With Oxygen Nucleophiles With Nitrogen Nucleophiles With Sulphur Nucleophiles With Carbanions Reduction and Elimination Reactions Thermal and Photochemical Reactions Reactions with Organometallic Compounds Miscellaneous Reactions 9 11 15 19 21 22 22 23 25 25 28 28 30 33 34 38 39 3 Aziridines Preparation By Direct Insertion 40 40 40 1 3 5 7 Heterocyclic Chemis0 viii By Cyclization Reactions By Ring-contraction Reactions Synt