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ADVANCES IN STRAINED AND INTERESTING ORGANIC MOLECULES Volume 8 This Page Intentionally Left Blank 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 This Page Intentionally Left Blank 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