Acetylene Chemistry. Chemistry, Biology And Material Science

Acetylene Chemistry Chemistry, Biology and Material Science Edited by F. Diederich, P. J. Stang, R. R. Tykwinski Acetylene Chemistry Edited by F. Diederich, P. J. Stang, R. R. Tykwinski Further Reading from Wiley-VCH A. de Meijere, F. Diederich (Eds.) Metal-Catalyzed Cross-Coupling Reactions, 2nd Ed., 2 Vols. 2004, ISBN 3-527-30518-1 R. Mahrwald (Ed.) Modern Aldol Reactions, 2 Vols. 2004, ISBN 3-527-30714-1 N. Krause, A. S. K. Hashmi (Eds.) Modern Allene Chemistry, 2 Vols. 2004, ISBN 3-527-30671-4 R. Gleiter, H. Hopf (Eds.) Modern Cyclophane Chemistry 2004, ISBN 3-527-30713-3 Acetylene Chemistry Chemistry, Biology and Material Science Edited by F. Diederich, P. J. Stang, R. R. Tykwinski Editors: Prof. Dr. Franois Diederich Laboratorium fr Organische Chemie ETH Hnggerberg, HCI CH-8093 Zrich Switzerland Prof. Dr. Peter J. Stang Department of Chemistry University of Utah 315S 1400E, Rm. 2020 84112 Salt Lake City USA Prof. Dr. Rik R. Tykwinski Department of Chemistry University of Alberta T6G 2G2 Edmonton Canada All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate. Library of Congress Card No.: applied for British Library Cataloguing-in-Publication Data: A catalogue record for this book is available from the British Library. Bibliographic information published by Die Deutsche Bibliothek Die Deutsche Bibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data is available in the Internet at . c WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2005 All rights reserved (including those of translation in other languages). No part of this book may be reproduced in any form – by photoprinting, microfilm, or any other means – nor transmitted or translated into machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law. Printed in the Federal Republic of Germany. Printed on acid-free paper. Typesetting hagedorn kommunikation, Viernheim Printing betz-druck gmbh, Darmstadt Bookbinding Litges & Dopf Buchbinderei GmbH, Heppenheim ISBN 3-527-30781-8 Preface The carbon-carbon triple bond is a common structural motif in organic chemistry. Only during the past two decades, however, has it become a mainstay in the toolbox of synthetic organic chemists, biochemists, and materials scientists. Both as a building block and as a versatile synthon, the fascinating and sometimes unpredictable chemistry associated with the alkyne moiety has fueled many of the most recent advances. A decade ago, the monograph Modern Acetylene Chemistry documented an emerging renaissance in the chemistry of the carbon-carbon triple bond. Over the past ten years, this renaissance has evolved at an astounding rate and acetylenes now constitute a principal class of compounds in nearly all areas of chemistry and materials science. The explosive growth of acetylene chemistry has particularly benefited from the development of new synthetic methodology based on transition metal catalysts and metal acetylides. An acetylene unit can now be introduced into nearly any desired molecule, large or small, often with surprising ease. Metal acetylides are key components for generating new nucleophilic reagents suitable for asymmetric addition reactions into electrophilic multiple bonds. The chemistry of early transition metal acetylides is especially rich, providing a fascinating class of compounds with remark