Advances in Physical Organic Chemistry Volume 42 Editor J. P. RICHARD Department of Chemistry University at Buffalo, SUNY Buffalo, NY 14260-3000, USA Amsterdam – Boston – Heidelberg – London – New York – Oxford Paris – San Diego – San Francisco – Singapore – Sydney – Tokyo Academic Press is an imprint of Elsevier ACADEMIC PRESS Academic Press is an imprint of Elsevier 84 Theobald’s Road, London WC1X 8RR, UK Radarweg 29, PO Box 211, 1000 AE Amsterdam, The Netherlands Linacre House, Jordan Hill, Oxford OX2 8DP, UK 30 Corporate Drive, Suite 400, Burlington, MA 01803, USA 525 B Street, Suite 1900, San Diego, CA 92101-4495, USA First edition 2008 Copyrightr 2008 Elsevier Inc. All rights reserved No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means electronic, mechanical, photocopying, recording or otherwise without the prior written permission of the publisher Permissions may be sought directly from Elsevier’s Science & Technology Rights Department in Oxford, UK: phone (+44) (0) 1865 843830; fax (+44) (0) 1865 853333; email: [email protected] Alternatively you can submit your request online by visiting the Elsevier web site at http://www.elsevier.com/locate/permissions, and selecting Obtaining permission to use Elsevier material Notice No responsibility is assumed by the publisher for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions or ideas contained in the material herein. Because of rapid advances in the medical sciences, in particular, independent verification of diagnoses and drug dosages should be made ISBN: 978-0-12-374093-9 ISSN: 0065-3160 For information on all Academic Press publications visit our website at books.elsevier.com Printed and bound in Great Britain 08 09 10 11 12 10 9 8 7 6 5 4 3 2 1 Contents Editor’s Preface ix Contributors to Volume 42 xi Cycloaromatization reactions: the testing ground for theory and experiment 1 IGOR ALABUGIN, BORIS BREINER and MARIAPPAN MANOHARAN 1 2 3 4 5 6 7 Introduction: bonds lost and bonds formed, or chemical bookkeeping 1 Cycloaromatization reactions: breaking p-bonds and breaking th