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~) ...... 200
XXXVI. Dinaphtho-( 1'.7': 2.18); (7".1": 9.11 )-heptacene l~y~J):) I~~~~~) ~~/ ...... 201
XXXVII. 7.8,17.18-Dibenzoctacene /~ ~~(']~~~~~ l)v0~1~1~100 I I ~/ ...... 204
CHAPTER 32. Hydrocarbons derived from Anthanthrene: I. Anthanthrene /~/~~ !i~I~ ~~/~ ...... 206
II. 1. 2,7.8-Dibenzanthanthrene /~ /~~~/I /I~)~/I~) fl~~) ~ ...... 208 xxvi CONTENTS
...... 2ll
IV. 2.3,8.9-Dibenzanthanthrene
. . . 213
V. 1.2-Benzonaphtho-(2".1": 7.8)-anthanthrene, Dinaphtho-(2'.l' :1.2); (2".1": 7.8)-anthanthrene and Dinaphtho-(1'.2' :1.2); (1".2": 7.8)-anthanthrene /~ I/~(~ I ~/~/~~/ I I I I /~~(~ (01W ~ I~~~) ~/~/ ~~// /~ I I ~/~ I I I~(/~II/ /~/""---/""---/
I 1 1 I 10",,---/~/""---/""---/ 1 I ~/ ...... 215
VI. 1.2-Benzophenanthreno-(10".2" :8.10)-anthanthrene (YYYYi /""---~~~~/""---/
I I 1 1 1 1 ~~~/~~ ...... 217 CONTENTS xxvii
OHAPTER 33. Hydrocarbons derived fromp-Terphenyl: 1. p-Terphenyl 9 2 I~ I ...... 221
...... 224
CHAPTER 34. Hydrocarbons derived from Terrylene: 1. Terrylene
...... 226 xxviii CONTENTS II. 7.8-Benzoterrylene
...... 230
III. 1.2,13.14-Dibenzoterrylene (10 C?X
o~ ...... 232
IV. 7.8,15.16-Dibenzoterrylene CONTENTS XXIX
CHAPTER 35. Hydrocarbons derived froID 2.3-peri-Naphthylenepyrene: 1. 2.3-peri-Naphthylenepyrene D? Xx 1~/)0 ...... 236
II. Pyreno-(l'.3' :l0'.2')-pyrene ITI/'--..../~
CrY ...... 237
III. 1.12,2.3,6.7,8.9-Tetrabenzanthanthrene
...... 239
IV. 9.1O,3'A'-Dibenzopyreno-(1.3:1O'.2'}-pyrene ID?J J?¢y ~~~ ...... 240 xxx CONTENTS
CHAPTER 36. Hydrocarbons derived from Peropyrene: I. /,Peropyrene M XX
W~/ ...... 242
II. 1.2,8.9-Dibenzoperopyrene
/~)~ 1109" 00 l)~ I i ~ ...... 246
III. 1.2,9.10-Dibenzoperopyrene II 03 I I 9))
~C)...... 251 CONTENTS XXXI IV. 1.2,6.7-Dibenzoperopyrene and 1.2,11. 12-Dibenzoperopyrene
V. 4.5,11.12-Dibenzoperopyrene /~ i I /~/~~ I~)~/I~/I ~)~~ I~/I~/I~) l) ...... 257
VI. 4.5,6.7,11.12,13.14-Tetrabenzoperopyrene /~ ('r/~~I ~/~/~~~/ I I /~/~/~/~ I I I I I ~/~/~/~/
I~/ I ...... 258 JI-b xxxii CONTENTS VII. 5.6,12.13-Dibenzoperopyrene /'--..- I I (~/~ /"I)~)~ I I I I l/I/~I/ "'/~/ I~) ...... 260
VIII. 2.3,5.6,8.9-Tribenzoperopyrene l/l/~ 1/11/r/i YYi "11/ /~/
I~/ I ...... 263 CONTENTS xxxiii X. 1.14,IO.1l-Dibenzoperopyrene /~/~ /l)",) I I I ~(y 1 " 9~x) ...... 266
XI. 3.4,5.6,7.8-Tribenzoperopyrene I~ ITIy:x ~)~)
I~/~/ I I ...... 268
XII. 3.4,5.6,IO.II,12.13-Tetrabenzoperopyrene II~I /~/~/ ~I I U:):) I I I /~~/ I~)~) ...... 269 XXXIV CONTENTS XIII. Dinaphtho-(7'.I': 1.13); (1".7": 6.8)-peropyrene
/ ...... / ...... CO:)
CD?~...... / ...... 271
XIV. Dinaphtho-(7'.I': 1.13); (1".7": 9.11 )-peropyrene
/ M...... / ...... / yx) / ...... ~ I I I I ~/~/ ...... / I...... ~/ I I ...... 273
XV. Dinaphtho-(I'.7' :2.4); (1".7": 9.11)-peropyrene and Dinaphtho-(I'.7': 2.4); (2".8": 7.9)-peropyrene CONTENTS xxxv XVI. Dinaphthoperopyrenes /~/~ I I I (I/~ /~~ '00 /l~ i I I ~~ ~~) I I I ~/~
PART V peri-Condensed Hydrocarbons consisting only of Six-membered Rings and Derived from Fundamental Systems with Four Benzenoid Rings CHAPTER 37. Hydrocarbons derived from Quaterphenyl: Quaterphenyl /~ I~) I I:)
...... 281 xxxvi CONTENTS
CHAPTER 38. Hydrocarbons dCl'i ved from Quaterrylene 1. Quaterrylene /i/~ I~/~) ~~ I~/~) ~~ ~~/ I/i/i1 1 ~/~/ ...... 283 II. 1.20,16.17-Dibenzoquaterrylene I/~I/i ~/~/~ I I I I/i~/ ~/~/ /~)~
1 I 1 ~/~/~
1 1 1 /~/~/ I~)~) ...... 284
CHAPTER 39. Hydrocarbons derived from 2.3,7 .8-Di-(pe1'i-naphthylene)• pyrene: 1. 2.3,7 .8-Di-(peri-naphthylene)-pyrene II~ ~I/i~ I/il CY~/
I 1
(,J:) ...... 286 CONTENTS xxxvii II. Dipyreno-(l'3' :10.2); (1".3": 5.7)-pyrene II~I ~~~ I~~ ~~~ ~~/I I"'-.)~/I~
1"'-./~/ 1 1 ...... 287
PART VI peri-Condensed Hydrocarbons consisting only of Six-membered Rings and Derived from Fundamental Systems with Five and Six Benzenoid Rings
CHAPTER 40: Quinquiphenyl and Sexiphenyl ~ 1",,/1 ¢ X~ 1 1 ~X "'-./.1 1 ...... 291, 292 xxxviii CONTENTS
PART VII peri-Condensed Hydrocarbons consisting of Six- and Five-membered Rings in which no Carbon Atom Is Linked with more than One Hydrogen Atom
CHAPTER 41. Hydrocarbons containing one Five-membered Ring: 1. Fluoranthene
II. 2.3-Benzofiuoranthene C) /~A'/l I'-----/"--../ 1 1 '---./ I ...... 303
III. 2.3,6.7-Dibenzofiuoranthene
<->/ \ 11/"--..1/"--..1/1 "--../'---./"--../"--../ ...... 306
IV. 3.4-Benzofiuoranthene
309 CONTENTS xxxix V. 10.1l-Benzofluoranthene /-\ \ /\ \_1 I~.)I ~~~...... 312
VI. 11.12-Benzofluoranthene
...... 315
VII. 3.4,11.12-Dibenzofluoranthene
...... 317
VIII. 9.1O,1l.12-Dibenzofluoranthene 1-\ 1-\ \_1)---1
(0 ...... 319 IX. 2.3,6.7,10.11-Tribenzofluoranthene
...... 320 xl CONTENTS X. Naphtho-(l'.2':2.3)-fluoranthene and Naphtho-(2'.l' :2.3)-fluoranthene Q /~/~/~ I I I I ~/~/~(~i
.~/ ...... 321
XI. Naphtho-(2'.3': 3.4)-fluoranthene <-) ~/~ I I I ~/~/~ I I ~/~ I I ~/ ...... 322 XII. Naphtho-(2'.3' :lO.Il)-fluoranthene and Naphtho-(2'.3': 11.12)-fluoranthene
XIII. 1O.Il-Benzonaphtho-(2".3": 3.4)-iluoranthene /-\ \-\) /-\ /~/~ I I I ~/',,--./~ I I ~/~
I~/ I ...... 327 CONTENTS xli XIV. 2.3-Benzonaphthofluoranthenes ;-) 1-\ <~~- I~/~I~I ~~~ ...... 327
XV. 2.3-0-Phenylenepyrene i\ \_1 /~~"" ~~)
I~~. I I ...... 329
XVI.<-\ 2.3-0- Phenylene-4.5-benzopyrene /~ /~~"" I I I I I/I~I/""/ ~~ ...... , .... , ...... 331 XVII.o 2.3-0- Phenylenenaphtho-(2/1.3/1: 4.5)-pyrene /C..,)~~"" l~~~/I 1/ I 1 ~~...... 332 xlii CONTENTS
1 1 XVIII. 4 o.5-o-Phenylenenaphtho-(2 .3": 3.4)-pyrene (1/~r>'Y"1 I/I/I~~/ ,,/~ ...... 333
XIX. 2.13-Benzofluoranthene
...... 335
337
XXI. 2.13,11.12-Dibenzofluoranthene ~--~/" 1 I 1 I 1 "(yy~ ,,/,,/ ...... 338
OHAPTER 42. Hydrocarbons containing Two Five-membered R,ings: 1. 4.5-0-Phenylenefluoranthene Q 10,,/1 o ...... 339 CONTENTS xliii II. Isorubicene <-) /-\ /~/~/~ I I I I "<":J/~/-) \- ...... 340 III. 5.6,l1.12-Di-o-phenylenetetraceneo /~~~/~ 10~!y0
<--:; ...... 342
IV. Rubicene
Iil~ I I I ~/"<~ / \ \~ ...... 345
V. 2.3-Benzorubicene \) /-\ I/I~I~I~I ~/,, <~ ...... 348 VI. Dibenzorubicenes ...... , . 349 xliv CONTENTS VII. 2.3,7.8-Di-(o-phenylene)-pyrene-\ <_I /~~"--- CrY~/ O...... 351 VIII. Periflanthene ...... 352 IX. 1.16-Benzoperiflanthene ...... 355 CONTENTS xlv X. 10.1l-(peri-Naphthylene)-fluoranthene /'-...... ~)'7 1...... )\- c6 ...... 357 XI. 11.12-(peri-Naphthylene)-fluoranthene ('-...... I/"-...... I '-...... ('y C\ /"-...... /'-...... /~ U...... ) ...... 358 XII. 2. 3, 6. 7-Di-(peri-naphthylene)-naphthalene 0< ...... jii«.J <_I '-...... /'-...... /...... _) ...... 360 XIII. 1.2,3.4-Di-(peri-naphthylene)-anthracene ...... 361 XIV. 2. 3, 6. 7-Di-(peri-naphthylene)-anthracene /\ /\ )-/1111/)-( L)/'-...... /'-...... /'-...... /"\_I ...... 363 xlvi CONTENTS XV. Di-(o-phenylene)-phenanthrene <~/ \ I/" I CXC7 ...... 364 XVI. 2.3-0-Phenylene-4.5-per'i-naphthylenepyrene 365 CHAPTER 43. Hydrocarbons containing Three Five-membered Rings: Decacyclene 366 CHAPTER 44. Hydrocarbons containing four Five-membered Rings: 1.2,3.4,5.6,7.8-Tetra-(peri-naphthylene )-anthracene ctlJl> ~/~ ...... 369 CONTENTS xlvii PART VIn pet'i-Condensed Hydrocarbons consisting of Six-membered Rings in which One Carbon Atom Is Linked with Two Hydrogen Atoms CHAPTER 45: I. Perinaphthene 375 II. Benzanthrenes (lJ?; "---/"---/~/ ...... 385, 394, 395 III. Naphtho-(2' .1': 7.8)-perinaphthene /~ H2 I I ~~/'-...,/ 10~/U l) 400 IV. N aphtho-( l' .2': 7.8)-perinaphthene H2 II~II ~(I/~(I ~/ ~/ ...... 401 V. 2.3,7 .8-Dibenzoperinaphthene (XI):)H2 ~) ...... 404 xlviii CONTENTS VI. Naphtho-(2'.3': 7.8)-perinaphthene H2 11/11/"1 "I:)~~~ ...... 406 VII. 4.5,7.8-Dibenzoperinaphthene CXf)H2 Cr ...... 408 VIII. Coeranthrene /~~~9i 1 I I 1 ~~~ ...... 412 IX. Naphthanthrene (1/" ~~~ I,,)~~I ...... 416 X. 3H-4.5- Benzonaphthanthrene I/~" I I 1~1~IIH2 "/~"C) ...... 418 CONTENTS xlix XI. 3.4-Benzonaphthanthrene /~/~ I I I /~~~/~ I~~~~ I I I I ...... 420 H2 XII. 1.2,IO.Il-Dibenzonaphthanthrene l/~I I~I ~~/~ I I I /~~/~ I~~~ I I I ...... 422 H2 XIII. 2.3-Benzonaphtho-(21 .3": 7.8)-perinaphthene (I ~~/~~/~ I~~~/~/~ I I I I I ...... 423 H2 XIV. 7.8-Benzonaphtho-(2 1 .3": 4.5)-perinaphthene /~ (y /~ /~~/I~ I~~~/ I I I ...... 424 Hz XV. 1.2,4.5,7.8-Tribenzoperinaphthene C:l ~J:~ 1~1~1~)", Hz I I "'/ ...... 426 CONTENTS XVI. 7 .8-Benzonaphtho-( 1".2" :4.5)-perinaphthene fX) /"'~~ I I I I ~~~H2 ...... 428 XVII. Anthraceno-(2'.3': 7.8)-perinaphthene ()~IH2 ...... 428 XVIII. 7 . 8-Benzanthraceno-(2". 3" : 4.5)-perinaphthene I~I (Y ~/ ~) ~~~ I I I I ~"'/~H2 ...... 430 PART IX peri-Condensed Hydrocarbons consisting of Six-membered Rings in which Two Carbon Atoms Are Linked with Two Hydrogen Atoms CHAPTER 46: I. 4.8-Dihydrotriangulene II H2(YIH2 1/1/1/1 "'/"'/"'/ ...... 433 CONTENTS Ii II. 5.6-Dihydro-1.12,1O.1l-dibenzotetracene Ii (I /~/~/~/"'--... 1 I I I I ~~ ...... /~ ...... 440 H2 f.[2 III. 3.1 I-Dihydro-l. 2,4.5, 6.7-tribenzotetracene I~ /~ (I/LA~H' ~/~~~"-, H2 1 I ~/ ...... 440 IV. 5.7-Dihydro-1.14,11.12-dibenzopentacene I~ 1/'1 ~~ O~ )C~)~~) 442 PART X Hydrocarbons consisting of Six-membered Rings which have Formally Fixed Double Bonds CHAPTER 47: 1. Zethrene /~/~ (f1 I I 0:) ...... 447 Iii CONTENTS ...... 449 III. 4.5,11.12-Dibenzozethrene I/~I I/~I/~I/ '-../~/ I I /~/ I I /~/~ I I I /~/'-../ I~ I ...... 451 IV. 5.6,l2.13-Dibenzozethrene /~/~(~ I I I 1/1/""/I I I /~/ I I I/I/~I/I ""/~~/ ...... 453 V. Heptazethrene I~I~I ""/~/ I I /~/ I I /""/ I I I/~I/I ""/~/ ...... 456 CONTENTS liii VI. 4.5,12.13-Dibenzoheptazethrene /~ I I /~~/~/~/~/~/~ I~I~L-I~I~L-I~I l/I ...... 458 VII. 5.6,13.14-Dibenzoheptazethrene /~/~/~ I I I I ~/.~/~/ I I #'~? I I /~? I I /~~/~ I~~~/ I I I ...... , ...... 461 PART XI Hydrocarbons consisting of Five- and Six-membered Rings which Have Formally Fixed Double Bonds CHAPTER 48: I. Indeno-(2'.1'/, :1.2)-perinaphthene uoo ...... 467 II. 1.2,4.5-Dibenzopentalene I:)~U:~J ...... 468 liv CONTENTS III. Dianthraceno-( 1'.D': 1.3); (1".9": 4.G)-pentalene /~/~~ I I I) ~Y~I /l)~~ I~~/~ I I I ...... 471 AUTHOR INDEX. . . . • ...... • ...... • . 473 Contents of Volume I PART I General CHAPTER 1. Nomenclature of Polycyclic Hydrocarbons CHAPTER 2. Carbon Atoms, p-Electrons and Hybridization CHAPTER 3. The C=C Double Bond and Conjugation in Butadiene CHAPTER 4. Theories about the Aromatic Bonds in Benzene CHAPTER 5. The Significance of Double Bonds and KekuIe Structures for the Stability of Aromatic Systems CHAPTER 6. The Aromatic Sextet and its Significance in Relation to the Stability of Aromatic Systems CHAPTER 7. The Annellation Principle CHAPTER 8. Asymmetric Annellation Effects CHAPTER 9. The Relation between p-, cx;- and f3-Bands, Phosphorescence Bands and the Reactive p-State in Aromatic Hydrocarbons CHAPTER 10. The Ionization Potentials and the Electronic Levels of the Aromatic Sextet CHAPTER 11. The Tautomerism of Phenols CHAPTER 12. The Relation between Hydroquinols and Quinones CHAPTER 13. Magnetic Properties of Aromatic Hydrocarbons CHAPTER 14. The Electrical Conductivity of Aromatic Hydrocarbons CHAPTER 15. The C-C Bond Length in Polycyclic Hydrocarbons CHAPTER 16. Non-coplanar, Overcrowded Aromatic Hydrocarbons CHAPTER 17. The Possibility of Bond Fixation by Substitution CHAPTER 18. Carcinogenesis by Polycyclic Aromatic Hydrocarbons and Certain Other Carcinogens, by Regina Schoental CHAPTER 19. General Methods for the Preparation of Aromatic Hydro• carbons Iv Ivi CONTENTS OF VOLUl\lE 1 PART II kala-Annellated Hydrocarbons CHAPTER 20. Benzene CHAPTER 21. Hydrocarbons Containing up to Two Linearly Annellated Benzene Rings: I. Naphthalene II. Phenanthrene III. Triphenylene IV. Chrysene V. 3.4-Benzophenanthrene VI. 1.2-Benzochrysene VII. Picene VIII. 5.6-Benzochrysene IX. 3.4,5.6-Dibenzophenanthrene X. Hexahelicene XI. 1.2,7.8-Dibenzochrysene XII. 11.12,13.14-Dibenzopicene XIII. 1.2,3.4,5.6,7.8,9.10, 11.12-Hexabenzotriphenylene CHAPTER 22. Hydrocarbons Containing Three Linearly Anellated Benzene Rings: I. Anthracene II. Tetraphene III. 1.2,3.4-Dibenzanthracene IV. 1.2,5.6-Dibenzanthracene V. 1. 2,7.8-Dibenzanthracene VI. 1.2,3.4,5.6-Tribenzanthracene VII. 1.2,3.4,5.6,7.8-Tetrabenzanthracene VIII. 1. 2-Benzotetraphene IX. 3.4-Benzotetraphene X. 3.4,8.9-Dibenzotetraphene XI. Pentaphene XII. 3.4-Benzopentaphene XIII. 3.4,9.10-Di benzopenta phene XIV. 1.2,5.6-Dibenzotetraphene XV. 6.7-Benzopentaphene XVI. Dinaphtho-(2'.I' :1.2) ;(2".1": 5.6)-anthracene XVII. Naphtho-(2'.3': 6. 7)-pentaphene XVIII. Naphtho-(2'.3': 3.4)-pentaphene CONTENTS OF VOLUME 1 Ivii XIX. Anthracel1o-(2'.1': 1.2)-anthracene XX. Anthracello-(~'.l': 8.H)-tetraphene XXI. Tetrapheno-(U' .S': S. D)-tetraphene XXII. ~.3-Bellzopicelle XXIII. ~.3,8. 9-Dibel1zopicene XXIV. Anthraceno-(I'.2' :1.2)-tetraphene CHAPTER 23. Hydrocarbons with Four Linearly Anl1ellated Benzene Rings: I. Tetracene II. 1.2-Benzotetracene III. 1.2,3.4-Dibenzotetracene IV. 1. 2,7.8-Dibenzotetracene V. 1.2,9.10-Dibenzotetracene VI. 1.2,3.4,7.8-Tribenzotetracene VII. 1.2,3.4,7 .8,9.10-tetrabenzotetracene VIII. Hexaphene IX. Heptaphene X. 7.8-Benzoheptaphene CHAPTER 24. Hydrocarbons with Five Linearly Annellated Rings: I. Pentacene II. 1.2-Benzopentacene III. 1.2,3.4-Dibenzopentacene IV. 1.2,8.9-Dibenzopentacene ancl1.2,lO.1l-Dibcnzopentiteene V. 1.2,3.4,8.9,lO.II-Tetrabenzopentacene CHAI"l'ER 25. Hydrocarbons with Six Linearly Annollatecl Rings: I. Hexacene II. 1.2-Benzohexacene CHAPTER 26. Hydrocarbons with Seven Linearly Annellated Rings: Heptacene CHAPTER 27. Hydrocarbons with Eight and More Linearly Annellated Rings: I. Octacene II. Nonacene III. Undecacene AUTHOR INDEX