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Polycyclic Hydrocarbons Polycyclic Hydrocarbons Volume 2 To Sir Robert Robinson Polycyclic Hydrocarbons E. CLAR University of Glasgow, Scotland With a chapter on Carcinogenesis by REGINA SCHOENT AL Medical Research Council, Cm"shaltan Surrey, England VOLUME 2 1964 Springer-Verlag Berlin Heidelberg GmbH ACADEMIC PRESS INC. (LONDON) LTD Berkeley Square House Berkeley Square London, W.1 ISBN 978-3-662-01670-1 ISBN 978-3-662-01668-8 (eBook) DOI 10.1007/978-3-662-01668-8 U.S. Edition published by ACADEMIC PRESS INC. 111 Fifth Avenue New York 3, New York Copyright © 1964 By SPRINGER-VERLAG BERLIN HEIDELBERG ORTGINALL Y PUBLTSHED BY ACADEMIC PRESS INC. (LONDO:t'<) LTD IN 1964 AU Rights Reserved No part ofthis book may be reproduced in any form, by photostat, microfilm, or any othcr means, without written permission from the publishers Library of Congress Catalog Card Number: 63-12392 Preface Polycyclic hydrocarbons are of interest in many fields of science: theoretical chemistry, physical chemistry, organic chemistry, dyestuff chemistry and biology. With regards to the latter, I am indebted to Dr. Regina Schoental of the Medical Research Council for the review in this present work of carcinogenesis by polycyclic hydrocarbons. This book is designed to present the facts in a simple and clear order and to derive empirical rules from them, but it does not present a com­ prehensive theory about polycyclic hydrocarbons. An attempt is made instead to extend classical symbolism into modern structural chemistry. Thus extensive use is made of Robinson's aromatic sextet, which is applied in an uncompromising and strict way. This quasi-classical attempt is encouraged further by such completely unexpected dis­ coveries as those of Dewar benzene and of the electronic asymmetry of formally symmetric hydrocarbons. How difficult it is to break away from any established way of thinking has been admirably expressed by Kekule ("Organische Chemie", 1861, Part 1, page 4, translated from German): "All our ideas are based, to an extent much greater than we ordinarily believe, on those of our predecessors. Our accumulated experience, the notions of which our training has accustomed us to, of whatever kind they have been, influence the course of our thoughts far more than we are willing to admit; only too frequently the following of our regularly used, well trodden way of thinking leads to us overlook the simplest of correlations. " Great emphasis has been given to the comparison of the physical properties of polycyclic hydrocarbons, and in this work as in future research, I have been and shall be guided by another declaration of Kekule ("Organische Chemie", Part 1, page 158): "Of course it must be continually kept in mind that one purpose of scientific research is to ascertain the constitution of matter and therefore the positions of atoms; this, however, cannot be achieved unambiguously by studying chemical reactions but on the contrary, only by comparing the physical properties of the existing compounds." I am indebted to my colleagues Dr. T. H. Goodwin, Dr. J. C. Speakman and Dr. F. Schwarz for valuable advice and help and to Dr. A. McCallum and Mr. J. Stephen for checking the proofs. I also greatly appreciate the efforts of Academic Press to meet my wishes. E. CLAR University of Glasgow April 1964 v Contents PART III peri-Condensed Hydrocarbons consisting only of Six-membered Rings and derived from Fundamental Systems with Two Benzenoid Rings CHAPTER 28. Hydrocarbons derived from Diphenyl: I. Diphenyl i~1 ~/ I:) . 3 II. Fluorene ~ I I ~/\ I CH 2 ~/ I I ~ ..... 6 III. Biphenylene ~-/"f I~/I_I~ .. 11 IV. 1.2-Benzobiphenylene I~_I~/i-Ji ..................... 15 V. 2.3-Benzobiphenylene I-I~~ ~)-~~) ... 17 vii VIll CONTENTS VI. 1.2,7.8-Dibenzobiphenylene 18 VII. 2. 3,6. 7-Dibenzobiphenylene O:)~:) .... 19 VIII. Tetraphenylene, Hexaphenylene and Octaphenylene (1_(1 O-Q I~( (I :C~C ~\ /~ I~/I (J vl)~~ 22 CHAPTER 29. Hydrocarbons derived from Perylene: I. Perylene rI~1 &S 24 CONTENTS ix II. 1.2-Benzoperylene 36 III. 2.3-Benzoperylene 40 IV. 1.2,7.8-Dibenzoperylene rI~~ ~~ 1",)~~0 .... 42 V. 1.2,l0.1l-Dibenzoperylene ~;::I ~~~~ . .. 46 VI. 1.2,11.12-Dibenzoperylene rI~O 47 sII-a* ............ x CONTENTS VII. 1.2,5.6-Dibenzoperylene I~I~I ~/~ I I /~/~~~ I~/~~/~/ I I I I .................. 51 VIII. 1.2,5.6,7.S,11.12-Tetrabenzoperylene I~I/~I/I~I "--/~/~r~ I I I~I/~I/"--I~I ~/~/~/~/ . ., 52 IX. 2.3,S. 9-Dibenzoperylene X. 2.3,lO.1l-Dibenzoperyleno 56 CONTENTS XI XI. Dinaphtho-(2'.3': 2.3); (2".3": 8.9)-perylene I~I ""(I ""~/"1 I I I ""/~ I I III ~~(~ L) 59 XII. 1.12-Benzoperylene ~~ I I I ~/~/~ 111/I I I ~/~ ...................... 60 XIII. 1.12,2.3-Dibenzoperylene ~~ I I I ~~/~ I I I /~/~/ I I I ~/~/~ l) ......... 63 XIV. 1.12,2.3,8.9-Tribenzoperylene II ~/~/~ I I I ""/"1~ I I I /~(~/ ! I ~~/~ I I ~/ ................... 65 xii CONTENTS xv. 1.12,2.3,10.11-Tribenzoperylene V"----/"----~ &6 .................... 66 XVI. 1.12,4.5,8.9-Tribenzoperylene ~ I"----)~l I I~ )yl~ I I rI~/ ~ ........................ 69 XVII. 1.12,5.6,7 .8-Tribenzoperylene rI~11 ~YYI ~~~/ I I I I "----/~~ ................... 71 72 CONTENTS xiii XIX. Anthraceno-( 1',4' :1.12)-perylene !I~I YY"("(i III~~/ ~~ ..................•..•• 73 XX. 1.12-0-Phenylene-2.3-benzoperylene 1:):)"(,, I I ) III~ ~Y"I ,,/ ...... • . • • . •• 75 XXI. 1.12-0-Phenylene-2.3,10 .11-dibenzoperylene 76 XXII. 1.2,3.4,5.6,10.11-Tetrabenzanthanthrene 78 xiv CONTENTS XXIII. Coronene /~(X~ ~ I I I I ~(yy ~~/ ..................... 79 XXIV. 1.2-Benzocoronene 86 XXV. 1.2,5.6-Dibenzocoronene /'- /~/II ~;C~ i I I I Y~./~/I I ~~I~I ~/ .................. " 88 XXVI. 1.2,7.8-Dibenzocoronene /~/~ rI~I~~1 ~~/~/~/~/ I~/~/ I I ................... 90 CONTENTS xv XXVII. 1.2,3.4,5.6-Tribenzocoronene (yy Cf(YO ~~/~ 1~ 1 .................... 92 XXVIII. Naphtho-(2'.3' :1.2)-coronene /~'---.... 1 I I II/'---....I/'---....I~I~I ~/'---..../~/'---..../'---..../ 1 I~/~/ I ..................... 94 XXIX. 1.12,2.3,4.5,6.7,8.9,10.11-Hexabenzocoronene (I I/'''-I~I/I~I ~('---..../'---....(~/ I I I !/'---....I/I/I 0'---....('---..../~ ~) ..................... 95 CHAPTER 30. Hydrocarbons derived from Bisanthene: I. Bisanthene I/'---....i/'---....I/~I '---....(I/Y 1/'---....1/'---....11 ~/'---..../'---..../ .................... 98 XVI CONTENTS II. 1.14-Benzobisanthene 07\ ~. 100 III. Ovalene IV. 3.4, 10. ll-Dibenzobisanthene and 3.4,1 I. 12-Dibenzobisanthene V. 1.2,3.4,8.9,10.1l-Tetrabenzobisanthene /~ c/I~ oYX~yY0 ~/ ................... 107 CONTENTS xvii VI. Circumanthracene 108 CHAPTER 31. Hydrocarbons derived from Pyrene: I. Pyrene (I 1('''-1 "-/~ l) ....................... llO II. 1.2-Benzopyrene ~ l)'~ . 127 III. 3.4-Benzopyrene (I 9 "- 130 IV. 1.2,3.4-Dibenzopyrene T~~ I,,-/. 1 . 141 XVlll CONTENTS V. 1.2,4.5-Dibenzopyrene /~ I I /~/~/~ I I I I !?/~ ~ ......... 145 VI. 1.2,6.7-Dibenzopyrene /~ /~/l/l~ I I I I I ~/~/~/~/ I I ~/ ... .. 148 VII. 3.4,8.9-Dibenzopyrene /~ I I ~/~ I I I/~I/~I '-,,/~/ I I ~/~ I I f} ~ ........ .. I I VIII. 3.4,9.10-Dibenzopyrene I~I /~/ I I /~/~ I I I ~/~/ I I ~~ I~/ I ....................... 153 CONTENTS XIX IX. 1.2,4.5,8.9-Tribenzopyrene ~ ¢y~ /~/ I~ I ......................... 157 X. 1.2,3.4,9.10-Tribenzopyrene /~ )~) I I I~~~ I I ~(I ~/ ...................... 160 XI. 1.2,3.4,6.7,8.9-Tetrabenzopyrene . .. 162 xx CONTENTS XII. Naphtho-(2'.3' :1.2)-pyrene cy=o(i l/ ........... 163 XIII. Naphtho-(I'.2': 3.4)-pyrene dI(" lX~ I~~I ....... 165 XIV. Naphtho-(2'.3': 3.4)-pyrene /" /l/I" I,,/,,/ I I I I If,,) ........... 166 XV. 1.2-Benzonaphtho-(2".3": 4.5)-pyrene 01 -))"XA/ O. 169 CONTENTS xxi XVI. 1.2-Benzonaphtho-(21 .3": 6.7)-pyrene ~~~/" 1~1""/J0,,,/J0 I"'/ I . .. 171 XVII. 8.9-Benzonaphtho-(21 .1":3.4)-pyrene and 3.4-Benz­ anthraceno-(2 1 .1": 8.9)-pyrene C) ) . 173 XVIII. 3.4-Benzonaphtho-(21 .3": 8.9)-pyrene C)::c:C) '" l~X/I ...... .. 174 XIX. 3.4-Benzonaphtho-(21 .3": 9.10)-pyrene E I~ L:~ I",/. I . .. 175 xxn CONTENTS xx. Dinaphtho-(2'.3' :1.2); (2".3" :4.5)-pyrene ~ /I~)~~/~ I I I I I ~/~/~~/ I I /y/~/ u. .. 177 XXI. Dinaphtho-(2'.3' :1.2); (2".3": 6.7)-pyrene (X):XXXJ(~ l) ................... 179 XXIII. Dinaphtho-(2'.3': 3.4); (2".3": 9.10)-pyrene /() /~)~) I I I (I~(I(I/ u~/~~ ................. 182 CONTENTS XXUl XXIV. 1.2-Benzodinaphtho-(2" .3": 4.5); (2" .3": 8. 9)-pyrene /~ ~) /0"l) I I I I~I~I/II/ ~/~~~/~ I~/ I ................. 183 XXV. 1.14,4.5-Dibenzopentacene /~ I I I/~I/~!/~I/~Iy~ ~~/~/'-y/ l/ ... " .......... 185 XXVI. Naphtho-(I'.7': 2.14)-pentacene /~/~ I I I l/I/~I/~I/I~I/ ~~~/~~/. 186 XXVII. Phenanthreno-(2' .3': 3.4)-pyrene ~~ I I I I,/~(~(~(~/ . I I/~I~/~~/ ~ ......................... 188 XXVIII. 1.2-Benzophenanthreno-(9'.10': 6.7)-pyrene /~ /~ I I I I ~~~~/ I I I I I ~/~/~/~/~ I~/ I I~/ I ................. 190 xxiv CONTENTS XXIX. 1.2,3.4,6.7, 12. 13-Tetrabenzopentacene (I / o:;cD " ~) ,,) . 191 XXX. 1.16,4.5-Dibenzohexacene (I CXXXX?J . .. 192 . 194 XXXII. Naphtho-(I'.7': 2. 16)-hexacene (Y" CI/"~/"~(") I I I I ~~~~~. ......... 195 XXXIII. 6.7,16.17-Dibenzoheptacene (I (I~I~('I~II ~"/"/YI/~"/ ,,/ . .. 197 XXXIV. 5.6,8.9,14.15,17.18-Tetrabenzoheptacene (I (I rII~('Y"I~(I ~YY"/YI/ ,,/ ,,/ ........... 198 CONTENTS XXV xxxv. 1.18,4.5,9.10,13.14-Tetrabenzoheptacene /~ (~ I~~/~/~~~~/~ l) I~) ...........
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