Compendium Of Organic Synthetic Methods, Volume 9

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E-Book Overview

Organic transformations are the heart of synthetic organic chemistry. The Compendium of Organic Synthetic Methods series facilitates the search for the most useful functional group transformations in organic chemistry. Compendium of Organic Synthetic Methods, Volume 9, provides quick access to proven protocols for the newest, most useful reactions and transformations. It contains both functional group transformations and bond-forming reactions, and focuses on the use of reagents readily available or easily prepared and handled in the laboratory.This valuable desktop resource contains over 1,200 examples of published reactions for the preparation of monofunctional compounds in a handy reference, as well as over 800 examples of difunctional compounds, and features over 30 more reviews than Volume 8. As in all the previous Compendium volumes, the classification schemes used allow for quick and easy reference and information retrieval. Chemical transformations are classified by the reacting functional group of the starting material and then by the functional group formed. Helpful indices are provided for both monofunctional and difunctional compounds as an efficient means of guidance to specific classes of transformations.Compendium of Organic Synthetic Methods, Volume 9, is an unparalleled source of information on the methods, reactions, and transformations in contemporary organic chemistry for the working chemist and student.Volume 9 in the series originated by I. T. Harrison and S. Harrison

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Compendium of Organic Synthetic Methods This page intentionally left blank Compendium of Organic Synthetic Methods Volume 9 MICHAEL B. SMITH DEPARTMENT OF CHEMISTRY THE UNIVERSITY OF CONNECTICUT STORRS, CONNECTICUT A Wiley-Interscience Publication JOHN WILEY & SONS, INC. New York Chichester Weinheim Brisbane Singapore Toronto Cover illustration was adapted from "Disconnect By the Numbers: A Beginner's Guide to Synthesis" by M. B. Smith. Journal of Chemical Education, 1990, 67, 848-856. This book is printed on acid-free paper. © Copyright © 2001 by John Wiley & Sons, Inc. All rights reserved. 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 Sections 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, 222 Rosewood Drive, Davers, MA 01923, (978) 750-8400, fax (978) 750-4744. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 605 Third Avenue, New York, NY 10158-0012, (212) 850-6011, fax (212) 850-6008, E-Mail: [email protected] For ordering and customer service, call 1-800-CALL-WILEY. Library of Congress Cataloging Card Number: 71-162800 ISBN 0-471-14579-3 Printed in the United States of America 10 9 8 7 6 5 4 3 2 1 CONTENTS PREFACE ABBREVIATIONS INDEX, MONOFUNCTIONALCOMPOUNDS INDEX, DIFUNCTIONAL COMPOUNDS INTRODUCTION 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 PREPARATION OF ALKYNES PREPARATION OF ACID DERIVATIVES PREPARATION OF ALCOHOLS PREPARATON OF ALDEHYDES PREPARATION OF ALKYLS, METHYLENESAND ARYLS PREPARATION OF AMIDES PREPARATION OF AMINES PREPARATION OF ESTERS PREPARATION OF ETHERS, EPOXIDES AND THIOETHERS PREPARATION OF HALIDES AND SULFONATES PREPARATION OF HYDRIDES PREPARATION OF KETONES PREPARATION OF NITRILES PREPARATION OF ALKENES PREPARATION OF OXIDES PREP