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ADVANCES IN STRAINED AND INTERESTING ORGANIC MOLECULES
Volume 8
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ADVANCES IN STRAINED AND INTERESTING ORGANIC MOLECULES
Editor: BRIAN HALTON School of Chemical and Physical Sciences Victoria University of Wellington
VOLUME 8
Al PRESS INC. Stamford, Connecticut
Copyright © 2000 by JAI PRESSINC 100 Prospect Street Stamford, Connecticut 06904-0811 All rights reserved. No part of this publication may be reproduced, stored on a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, filming, recording, or otherwise without prior permission in writing from the publisher. ISBN: 0-7623-0631-9 ISSN: 1061-8902 Manufactured in the United States of America
CONTENTS LIST OF CONTRIBUTORS
vi i
PREFACE Brian Halton
ix
NATURAL AND NON-NATURAL PLANAR CARBON NETWORKS: FROM MONOMERIC MODELS TO OLlGOMERlC SUBSTRUCTURES Michael M . Haley and W. Brad Wan
1
RECENT DEVELOPMENTS IN STRAINED CYCLIC ALLENES Metin Balci and Yavuz Taskesenligil
43
STRAIN AND STRUCTURE OF STERICALLY CONGESTED TRIPLET CARBENES Hideo Tomioka
83
SYNTHESIS AND CHEMISTRY OF STRAINED CARBOHYDRATES: OXABICYCL0[4.1 .O]HEPTANES Ghislaine S. Cousins and John 0. Hoberg
113
EXPLOITING THE STRAIN IN 12.2.1IBICYCLIC SYSTEMS IN POLYMER AND SYNTHETIC ORGANIC C HEMISTRY Michael North
145
AZlRlNES AND AZlRlDlNES REVISITED Kuriya Madavu Lokanatha Rai and Alfred Hassner
187
INDEX
259
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LIST OF CONTRIBUTORS Metin Balci
Department of Chemistry Middle EastTechnical University Ankara, Turkey
Ghislaine 5. Cousins
School of Chemical and Physical Sciences Victoria University of Wellington Wellington, New Zealand
Michael M. Haley
Department of Chemistry University of Oregon Eugene, Oregon
Alfred Hassner
Department of Chemistry Bar-Ilan University Ramat-Gan, Israel
John O. Hoberg
School of Chemical and Physical Sciences Victoria University of Wellington Wellington, New Zealand
Michael North
Department of Chemistry King's College London, England
Kuriya Madavu Lokanatha Rai
Department of Chemistry University of Mysore Mysore, India
Yavuz Taskesenligil
Department of Chemistry Ataturk University Erzurum, Turkey
Hideo Tomioka
Chemistry Department for Materials Mie University Tsu, Mie, Japan vii
viii W. Brad Wan
LIST OF CONTRIBUTORS Department of Chemistry University of Oregon Eugene, Oregon
PREFACE The past year has seen the publication of the first Supplement to this Series under the editorship of Professor K. K. Laali and this signals our wish to provide timely collections under independent editorship from, for example, important international symposia. Carbocyclic and Heterocyclic Cage Compounds and Their Building Blocks appeared in June as the first Supplement of the past century---I sincerely hope that the next Supplement will not be the last of the present one! The present Volume, which comprises six chapters and involves ten authors from seven countries, provides a pot pourri of interesting strained and not so strained molecules and their use----or abuseBin the widest sense. Haley and Wan of the University of Oregon give a position summary of planar carbon networks. Their discourse commences with graphite and outlines methods now brought to bear on the synthesis of oligophenylenes, their conversions into polycyclic aromatic hydrocarbons such as "supernaphthalene" and "supertriphenylene," and the need to avoid alkyne "mismatch" that can lead to non-planarizable products. Next come polyphenylenes (or polyb