Compendium Of Organic Synthetic Methods -volume 6

Compendium of Organic Synthetic Methods Volume 6 MICHAEL B. SMITH DEPARTMENT OF CHEMISTRY UNIVERSITY OF CONNECTICUT STORRS, CONNECTICUT A Wiley-Interscience Publication JOHN WILEY & SONS New York 0 Chichester e Brisbane 0 Toronto 0 Singapore A NOTE TO THE READER This book has been electronically reproduced from digital information stored at John Wiley & Sons, Inc. We are pleased that the use of this new technology will enable us to keep works of enduring scholarly value in print as long as there is a reasonable demand for them. The content of this book is identical to previous printings. Copyright @ 1988 by John Wiley & Sons, Inc. All rights reserved. Published simultaneously in Canada. Reproduction or translation of any part of this work beyond that permitted by Section 107 or 108 of the 1976 United States Copyright Act without the permission of the copyright owner is unlawful. Requests for permission or further information should be addressed to the Permissions Department, John Wiley & Sons, Inc. Library of Congress Catalog Card Number: 71-162800 ISBN 0-471-84896-4 1 0 9 8 7 6 5 PREFACE It has been sixteen years since Ian and Shuyen Harrison first published the Compendium of Organic Synthetic Methods to facilitate the search for functional group transformations in the formidable body of the original literature. In Volume 2 this concept was expanded to include difunctional compounds. Louis Hegedus and Leroy Wade carried on this important compilation in Volume 3 and Wade continued with Volumes 4 and 5. Volume 6 is intended to continue the Harrisons’ stated purpose of “a comprehensive one-volume listing of synthetic methods as an intermediary between the chemist and the literature.” Compendium of Organic Synthetic Methods, Volume 6, presents the functional group transformations and difunctional compound preparations of 1983, 1984, 1985, and 1986. The classification schemes of the first five volumes have been followed but a new chapter has been added. Each literature citation now includes all authors and the text concludes with an Author Index. The new Chapter 15 classifies the oxides of nitrogen, sulfur, and selenium with section headings identical to Chapters 1-14. The difunctional compounds now appear in Chapter 16. The experienced user of the Compendium will require no special instructions for the use of the new oxides chapter or the complete volume. Author citations and the Author Index have been included to facilitate literature searches and to follow the current work of a particular author. The citations should not prove obtrusive and will hopefully assist the synthetic community . I wish to express my gratitude to Professor Michael Edwards who first suggested this project to me. I also wish to thank Professor Leon Ghosez who provided the facilities for a pleasant sabbatical leave, which allowed completion of the research for this text. My thanks to Tae Woo Kwon, Jennline Sheu, Royce Menezes, Chung Jen Wang, Paul Keusenkothen, and Young Chan Son who proofread parts of the manuscript and offered many helpful suggestions. I want to thank my wife Sarah and son Steven for their patience and moral support throughout this work. MICHAELB. SMITH Storrs, Connecticut June 1987 V CONTENTS ABBR EVIAT1ONS INDEX, MONOFUNCTIONAL COMPOUNDS INDEX, DIFUNCTIONAL COMPOUNDS INTRODUCTION 1 PREPARATION OF 2 PREPARATION OF AND ANHYDRIDES 3 PREPARATION OF 4 PREPARATION OF 5 PREPARATION OF 6 PREPARATION (2F 7 PREPARATION OF 8 PREPARATION OF 9 PREPARATION OF THIOETHERS 10 PREPARATION OF 11 PREPARATION OF 12 PREPARATION OF 13 PREPARATION OF 14 PREPARATION OF 15 PREPARATION OF 16 PREPARATION OF AUTHOR INDEX ACETYLENES CARBOXYLIC ACIDS, ACID HALIDES, ALCOHOLS, PHENOLS, AND THIOLS ALDEHYDES ALKYLS, METHYLENES, AND ARYLS AMIDES AM