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5,5 Systems with a Bridgehead Nitrogen Atom (J. P. Paolini). Indolizine and Aza-Derivatives with Additional Nitrogens in the Five-Membered Ring (H. L. Blewitt). Azaindolizine Systems Having More Than One Nitrogen Atom in the Six-Membered Ring (G. Maury). The Chemistry of Cyclazines (A. Taurins). Dithiole and Dithiolium Systems (R. D. Hamilton and E. Campaigne). Heteropentalenes (K. Potts). Borazaromatic Compounds (A. J. Fritsch). Syntheses and Properties of Cyanine and Related Dyes (D. M. Sturmer).Content: Chapter I 5,5?System With a Bridgehead Nitrogen Atom (pages 1–115): P. PaoliniChapter II Indolizine and Aza Derivatives With Additional Nitrogens in the 5?Membered Ring (pages 117–178): H. L. BlewittChapter III Azaindolizine Systems Having More Than One Nitrogen Atom in the 6?Membered Ring (pages 179–244): Georges MaueyChapter IV The Chemistry of Cyclazines (pages 245–270): Alfred TaurinsChapter V Dithiole and Dithiolium Systems (pages 271–315): R. D. Hamilton and E. CampaignsChapter VI Heteropentalenes (pages 317–379): K. T. PottsChapter VII Borazaromatic Compounds (pages 381–440): Albert J. FritschChapter VIII Syntheses and Properties of Cyanine and Related Dyes (pages 441–587): David M. Sturmer
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S P E C I A L TOPICS IN HETEROCYCLIC CHEMISTRY This is the thirtieth volume in rhe series T H E C H E M I S T R Y OF H E T E R O C Y C L I C C O M P O U N D S T H E CHEMISTRY OF HETEROCYCLIC COMPOUNDS A S t K l f i S 01 M O h O G R A P H S A R N O L D W E I S S B E R C E R rnd E D W A R D C. T A Y L O R Editors S P E C I A L TOPICS I N HETEROCYCLIC CHEMISTRY Edited by Arnold Weissberger Research Loboraiories Eastman Kodak Company Rochesrer, New York Edward C. Taylor Princeton Uniwrsiry Princeton, New Jersey AN INTERSCIENCEQPUBLICATION JOHN W l L E Y & S O N S N E W Y O R K . L O N D O N * S Y D N E Y . TOR ON TO An lnterscience @ Publication Copyright @ 1977 by J o h n Wiley & Sons, Inc. All rights reserved. Published simultaneously in Canada. No part of this book may be reproduced by any means, nor transmitted, nor translated into a machine language without the written permission of the publisher. Library of Co#gress Cataloging in Publicarion Dam: Main entry under title: Special topics in heterocyclic chemistry. (The Chemistry of heterocyclic compounds: v. 30) "An lnterscience publication." Bibliography: p. 1. Heterocyclic compounds-Addresses, essays, lectures. 11. Taylor, Edward 1. Weissberger, Arnold, 1898-. Curtis, 1923QDJOO.SS12 547'.59 76-10672 ISBN 0-471-67253-X 1 0 9 8 7 6 5 3 3 2 I Contributors H. L. Blewitt, Uniuersity of Alabama, Tuscaloosa, Alabama E. Campaigne, Ft. Lewis College, Durango, Colorado Albert 1. Fritsch, Center for Science in the Public Interest, Washington, D.C. R. D. Hamilton, Ff. Lewis College, Durango, Colorado Georges Mnury, Department de Chimie, Faculte' des Sciences, Rabat, Morocco John P. Paolini, Merrell -National Laboratories, Cincinnati, Ohio K. T. Potts, Department of Chemistry, Rensselaer Polytechnic Institute, Troy, New York David M . Stunner, Research Laboratories. Eastman Kodak Companv, Rochester, New York Alfred Taurins, Department of Chemistry, McGill University, Montreal, Canada The Chemistry of Heterocyclic Compounds The chemistry of heterocyclic compounds is one of the most complex branches of organic chemistry. It is equally interesting for its theoretical implications, for the diversity of its synthetic procedures, and for the physiological and industrial significance of heterocyclic compounds. A field of such importance and intrinsic difficulty should be ma