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1,2,3-Thiadiazoles are a group of heterocycles whose derivatives are important in industry, medicine, and agriculture. This volume provides a complete treatment of this group of heterocycles with an emphasis on syntheses, structural data, properties, reactions, and applications.
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THE CHEMISTRY OF 1,2,3-THIADIAZOLES
This is the sixty-second volume in the series THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS
THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS A SERIES OF MONOGRAPHS
EDWARD C. TAYLOR AND PETER WIPF, Editors ARNOLD WEISSBERGER, Founding Editor
THE CHEMISTRY OF 1,2,3-THIADIAZOLES
Vasiliy A. Bakulev Department of Technology for Organic Synthesis The Urals State Technical University
Wim Dehaen Department of Chemistry University of Leuven
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Copyright 2004 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 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 978-646-8600, 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., 111 River Street, Hoboken, NJ 07030, (201) 748-6011, fax (201) 748-6008. Limit of Liability/Disclaimer 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 please contact our Customer Care Department within the U.S. at 877-762-2974, outside the U.S. 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, however, may not be available in electronic format. Library of Congress Cataloging-in-Publication Data: Bakulev, Vasiliy and Dehaen, Wim The Chemistry of 1,2,3-Thiadiazoles ISBN 0-471-32662-3 Printed in the United States of America. 10 9 8 7 6 5 4 3 2 1
The Chemistry of Heterocyclic Compounds Introduction to the Series The chemistry of heterocyclic compounds is one of the most complex and intriguing branches of organic chemistry, of equal interest for its theoretical implications, for the diversity of its synthetic procedures, and for the physiological and industrial significance of heterocycles. The Chemistry of Heterocyclic Compounds has been published since 1950 under the initial editorship of Arnold Weissberger, and later, until his death in 1984, under the joint editorship of Arnold Weissberger and Edward C. Taylor. In 1997, Peter Wipf joined Prof. Taylor as editor. This series attempts to make the extraordinarily complex and diverse field of heterocyclic chemistry as organized and readily accessible as possible. Each volume has traditionally dealt with syntheses, reactions, properties, structure, physical chemistry, and utility of com