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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. Paolini Chapter II Indolizine and Aza Derivatives With Additional Nitrogens in the 5?Membered Ring (pages 117–178): H. L. Blewitt Chapter III Azaindolizine Systems Having More Than One Nitrogen Atom in the 6?Membered Ring (pages 179–244): Georges Mauey Chapter IV The Chemistry of Cyclazines (pages 245–270): Alfred Taurins Chapter V Dithiole and Dithiolium Systems (pages 271–315): R. D. Hamilton and E. Campaigns Chapter VI Heteropentalenes (pages 317–379): K. T. Potts Chapter VII Borazaromatic Compounds (pages 381–440): Albert J. Fritsch Chapter 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