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When Wittig first developed and described phosphorus ylides, nobody could have imagined how useful and versatile this class of compounds could be. This book provides a comprehensive and up-to-date compilation of the chemistry and applications of phosphorus ylides in organic synthesis. The ylides are discussed as reagents in the synthesis of a broad range of substances, amongst them olefins, acetylenes, cyclic and heterocyclic compounds, in such naturally occurring compounds as pheromones, steroids and carotenoids, and pharmaceutically and biologically active compounds such as antibiotics and prostaglandins. A particularly beneficial feature of this book is the 150 key experimental procedures with all the necessary data, allowing the preparation to start immediately without the need for an extremely time-consuming literature search. But should a search prove inevitable, around 2,500 references provide easy access to the primary literature. Every chemist in academia and industry working in organic, bioorganic, inorganic, and medicinal chemistry will welcome this book as an inspiration of concepts, ideas and practical syntheses.
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Oleg I. Kolodiazhnyi Phosphorus Ylides @ WILEY-VCH Further Titles of Interest K. Ruck-Braun, H. Kunz Chiral Auxiliaries in Cycloadditions 1999, ISBN 3-527-29386-8 F. Diederich, P. J. Stang (Eds.) Metal-catalyzed Cross-coupling Reactions 1998, ISBN 3-527-29421-X Y. Chapleur (Ed.) Carbohydrate Mimics Concepts and Methods 1998, ISBN 3-527-29526-7 H. A. Staab, H. Bauer, K. M. Schneider Azolides in Organic Synthesis and Biochemistry 1998, ISBN 3-527-29314-0 Oleg I. Kolodiazhnyi Phosphorus Ylides Chemistry and Application in Organic Synthesis @ WILEY-VCH Wcinheim - New York - Chichester Brisbane - Singapore * Toronto Prof. Dr. Oleg I. Kolodiazhnyi Institut of Bioorganic Chemistry National Academy of Sciences 1, Murmanskaya Street 253660, Kiev-94 Ukraine This book was carefully produced. Nevertheless, author and publisher do not warrant the information contained therein 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. I I Cover Illustration: Dr. A. Savin, Paris, France. Library of Congress Card No. applied for. A catalogue record for this book is available from the British Library. Deutsche Bibliothek Cataloguing-in-Publication Data: Kolodiazhnyi, Oleg I.: Phosphorus ylides : chemistry and application in organic synthesis I Oleg I. Kolodiazhnyi. - 1. Aufl. - Weinheim ; New York ; Chichester ; Brisbane ; Singapore ;Toronto : Wiley-VCH, 1999 ISBN 3-527-2953 1-3 0WILEY-VCH Verlag GmbH, D-69469 Weinheim (Federal Republic of Germany), 1999 Printed on acid-free and chlorine-free paper. All rights reserved (including those of translation in other languages). No part of this book may be reproduced in any forni - 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. Printing: betz-druck gmbh, D-64291 Darmstadt. Bookbinding: J. Schaffer GmbH & Co. KG., D-67269 Griinstadt. Printed in the Federal Republic of Germany. To my daughters, Anastasia and Olga Contents 1 2 and Structure of Book . . . . . . . . . . . . 3 . . . . . . . . . . . . . . . . . . . . . . . . 5 . . . . . . . . . . . . . . . . . . . . . . . . 7 1 1.1 1.2 1.3 Introduction . . . . . . . . Historiography . . . . . . . Typcs of' Phosphorus Ylidcs Nornenclaturc . . . . . . . . References . . . . . . . . . 2 2.1 2.1.1 2.2 2.2.1 2.2.1.1 2.2.