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Name Reactions of Functional Group Transformations (Comprehensive Name Reactions) PDF

770 Pages·2007·25.39 MB·English
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Name Reactions for Functional Group Transformations Edited by Jie Jack Li Pfizer Global Research & Development E. J. Corey Harvard University BICLNTENNIAL WILEY-INTERSCIENCE A John Wiley & Sons, Inc., Publication This Page Intentionally Left Blank Name Reactions for Functional Group Transformations THE WlLEY BICENTENNIAL-KNOWLEDGE FOR GENERATIONS G a c hg eneration has its unique needs and aspirations. When Charles Wiley first opened his small printing shop in lower Manhattan in 1807, it was a generation of boundless potential searching for an identity. And we were there, helping to define a new American literary tradition. Over half a century later, in the midst of the Second Industrial Revolution, it was a generation focused on building the future. Once again, we were there, supplying the critical scientific, technical, and engineering knowledge that helped frame the world. Throughout the 20th Century, and into the new millennium, nations began to reach out beyond their own borders and a new international community was born. Wiley was there, expanding its operations around the world to enable a global exchange of ideas, opinions, and know-how. For 200 years, Wiley has been an integral part of each generation's journey, enabling the flow of information and understanding necessary to meet their needs and fulfill their aspirations. Today, bold new technologies are changing the way we live and learn. Wiley will be there, providing you the must-have knowledge you need to imagine new worlds, new possibilities, and new opportunities. Generations come and go, but you can always count on Wiley to provide you the knowledge you need, when and where you need it! r 4 PRESIDENT AND CHIEF EXECUTIVE OFFICER CHAIRMAN OF WE BOARD Name Reactions for Functional Group Transformations Edited by Jie Jack Li Pfizer Global Research & Development E. J. Corey Harvard University BICLNTENNIAL WILEY-INTERSCIENCE A John Wiley & Sons, Inc., Publication Copyright 0 2007 by John Wiley & Sons, Inc. All rights reserved. Published by John Wiley & Sons, Inc., Hoboken, New Jersey. Published simultaneously in Canada. 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, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750-8400, fax (978) 750-4470, or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 11 1 River Street, Hoboken, NJ 07030, (201) 748-601 I, fax (201) 748-6008, or online at http://www.wiley.com/go/permission. Limit of LiabilityDisclairner of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages. For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at (800) 762-2974, outside the United States at (317) 572-3993 or fax (317) 572-4002. Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic format. For information about Wiley products, visit our web site at www.wiley.com. Wiley Bicentennial Logo: Richard J. Pacific0 Library of Congress Cataloging-in-Publication Data: Name reactions for functional group transformations / edited by Jie Jack Li, E. J. Corey. p. cm. Includes index. ISBN 978-0-471-74868-7 1. Organic compounds-Synthesis. 2. Chemical reactions. I. Li, Jie Jack. 11. Corey, E. J. QD262.N36 2007 547l.26~22 2007010254 Printed in the United States of America. 1 0 9 8 7 6 5 4 3 2 1 Dedicated To Li Wen-Liang and Chen Xiao-Ying This Page Intentionally Left Blank vii Foreword Part of the charm of synthetic organic chemistry derives from the vastness of the intellectual landscape along several dimensions. First, there is the almost infinite variety and number of possible target structures that lurk in the darkness waiting to be made. Then, there is the vast body of organic reactions that serve to transform one substance into another, now so large in number as to be beyond credibility to a non-chemist. There is the staggering range of reagents, reaction conditions, catalysts, elements, and techniques that must be mobilized in order to tame these reactions for synthetic purposes. Finally, it seems that new information is being added to that landscape at a rate that exceeds the ability of a normal person to keep up with it. In such a troubled setting any author, or group of authors, must be regarded as heroic if through their efforts, the task of the synthetic chemist is eased. Modern synthetic chemistry is a multifaceted discipline that greatly benefits from the development of unifying concepts. One of the most useful of these is the idea of the “functional group,” generally considered to be a specific collection of connected atoms that occur frequently in organic structures and that exhibit well defined and characteristic chemical behavior. The simplest and most common functional groups (e.g., C=C, CHO, OH, COOH, NH2) dominate the organization of entry-level organic chemistry textbooks and provide a framework for understanding the fundamentals of the subject. The more complex functional groups, formed using additional elements or by concatenation of simpler groups, play a similar unifying role. This volume, Name Reactions for Functional Group Transformations, provides a survey of important transformations that are characteristic of the whole range of functional groups and also serve to interconnect them. In the more than six hundred pages that follow, a highly qualified team of nineteen authors from academia and industry has provided an up-to-date account of forty-seven major classes of functional group transformations. The reviews are clear, concise, and well-referenced. This book serves as a fine companion to the first volume of this series, Name Reactions in Heterocyclic Chemistry. E. J. Corey November 13,2006

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"This comprehensive reference delves into the details of name reactions that are important to researchers. It presents an up-to-date account of forty-seven major classes of functional group transformations and also serves to interconnect them. The book includes reviews from leading scientists in the
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