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