24:
167:
389:
369:
431:
285:
298:
216:
1089:
388:
368:
181:
332:
rings fused onto it. This compound and related compounds are studied in the laboratory because they are often displaying unusual
682:
1094:
673:
630:
Toshiyuki Hamura, Yousuke
Ibusuki, Hidehiro Uekusa, Takashi Matsumoto, Jay S. Siegel, Kim K. Baldridge, and Keisuke Suzuki
305:
430:
991:
145:
403:
88:
23:
519:
824:
1104:
1099:
885:
880:
333:
870:
865:
860:
855:
778:
345:
321:
36:
162:
562:
534:
54:
399:
is 154 pm long. On the other hand, no change is recorded in the aromatic bond length alternation.
926:
666:
987:
763:
631:
616:
608:
565:
550:
515:
511:
487:
360:
977:
773:
768:
639:
573:
495:
363:
in 1979 by the following sequence: This compound is stable up to 250 °C (482 °F).
239:
108:
64:
542:
530:
564:
Toshiyuki Hamura, Yousuke
Ibusuki, Hidehiro Uekusa, Takashi Matsumoto, and Keisuke Suzuki
166:
1027:
1022:
936:
905:
839:
834:
727:
597:
276:
1083:
659:
589:
546:
972:
921:
803:
788:
747:
722:
651:
458:
133:
946:
931:
829:
706:
463:
453:
419:
395:
An ordinary bond of this type is only 148 pm and for comparison the C-C bond in
376:
329:
875:
844:
732:
526:
261:
99:
628:
1068:
1058:
1053:
982:
890:
798:
742:
448:
415:
380:
341:
1063:
1017:
1007:
997:
967:
951:
941:
895:
783:
737:
696:
538:
443:
418:. A key starting material is the iodo triflate depicted below which is a
499:
1032:
1012:
1002:
701:
422:
383:
for the bond connecting two carbonyl groups by the following sequence:
325:
120:
643:
577:
900:
793:
612:
604:
396:
337:
275:
Except where otherwise noted, data are given for materials in their
603:
and a ketene silyl acetal. The silyl acetal is then converted to a
1048:
593:
523:
336:
and because of their unusual reactivity. Tricyclobutabenzenes are
87:
77:
655:
150:
375:
A polyoxygenated tricyclobutabenzene with an extraordinary
190:
InChI=1S/C12H12/c1-2-8-7(1)9-3-4-11(9)12-6-5-10(8)12/h1-6H2
200:
InChI=1/C12H12/c1-2-8-7(1)9-3-4-11(9)12-6-5-10(8)12/h1-6H2
486:
Wutichai
Nutakul, Randolph P. Thummel, Austin D. Taggart
522:
with dimethylcyclobutene-1,2-dicarboxylate, followed by
293:
1041:
960:
914:
817:
756:
715:
689:
132:
63:
402:Similar chemistry yielded the six-fold ketone
667:
8:
674:
660:
652:
596:formed from the iodotriflate by action of
165:
107:
15:
476:
221:
186:
161:
588:Reaction sequence: the key step is a
193:Key: MTPUNWSZJLTTLU-UHFFFAOYSA-N
7:
203:Key: MTPUNWSZJLTTLU-UHFFFAOYAI
123:
14:
351:The parent tricyclobutabenzene (C
1090:Polycyclic aromatic hydrocarbons
683:Polycyclic aromatic hydrocarbons
429:
387:
367:
283:
251:
22:
279:(at 25 °C , 100 kPa).
414:, which happens to be a novel
245:
1:
41:Tetracyclododeca-1,5,9-triene
638:; 128(31) pp 10032 - 10033;
1121:
572:; 128(11) pp 3534 - 3535;
404:hexaoxotricyclobutabenzene
466:where the rings are fused
273:
232:
212:
177:
47:
35:
30:
21:
849:-Benzopyrene(Olympicene)
615:groups by reaction with
224:c12c4c(c3c(c1CC2)CC3)CC4
1095:Tetracyclic compounds
825:Benzacephenanthrylene
520:Diels–Alder reaction
322:aromatic hydrocarbon
37:Preferred IUPAC name
17:Tricyclobutabenzene
809:Tricyclobutabenzene
535:potassium hydroxide
510:Reaction sequence:
500:10.1021/ja00497a064
494:; 101(3); 770-771.
484:Tricyclobutabenzene
318:Tricyclobutabenzene
269: g·mol
18:
611:and the remaining
306:Infobox references
16:
1077:
1076:
988:Hexabenzocoronene
871:Benzofluoranthene
866:Benzofluoranthene
861:Benzofluoranthene
856:Benzofluoranthene
779:Benzophenanthrene
644:10.1021/ja064063e
632:J. Am. Chem. Soc.
617:boron trifluoride
609:hydrofluoric acid
578:10.1021/ja0602647
566:J. Am. Chem. Soc.
551:lead tetraacetate
516:Grignard reagents
512:coupling reaction
488:J. Am. Chem. Soc.
314:Chemical compound
312:
311:
146:CompTox Dashboard
89:Interactive image
1112:
978:Diindenoperylene
886:Dibenzanthracene
881:Dibenzanthracene
876:trans-Bicalicene
676:
669:
662:
653:
646:
625:
619:
586:
580:
559:
553:
508:
502:
481:
433:
391:
371:
328:core with three
324:consisting of a
296:
290:
287:
286:
268:
253:
247:
240:Chemical formula
170:
169:
154:
152:
136:
125:
111:
91:
67:
26:
19:
1120:
1119:
1115:
1114:
1113:
1111:
1110:
1109:
1080:
1079:
1078:
1073:
1042:General classes
1037:
956:
910:
813:
752:
711:
685:
680:
650:
649:
626:
622:
587:
583:
560:
556:
543:decarboxylation
531:carboxylic acid
514:of cyclobutene
509:
505:
482:
478:
473:
440:
416:oxide of carbon
413:
409:
358:
354:
315:
308:
303:
302:
301: ?)
292:
288:
284:
280:
266:
256:
250:
242:
228:
225:
220:
219:
208:
205:
204:
201:
195:
194:
191:
185:
184:
173:
155:
148:
139:
126:
114:
94:
81:
70:
57:
43:
42:
12:
11:
5:
1118:
1116:
1108:
1107:
1102:
1097:
1092:
1082:
1081:
1075:
1074:
1072:
1071:
1066:
1061:
1056:
1051:
1045:
1043:
1039:
1038:
1036:
1035:
1030:
1028:Trinaphthylene
1025:
1023:Superphenalene
1020:
1015:
1010:
1005:
1000:
995:
985:
980:
975:
970:
964:
962:
958:
957:
955:
954:
949:
944:
939:
937:Dibenzopyrenes
934:
929:
924:
918:
916:
912:
911:
909:
908:
906:Tetraphenylene
903:
898:
893:
888:
883:
878:
873:
868:
863:
858:
853:
852:
851:
842:
837:
827:
821:
819:
815:
814:
812:
811:
806:
801:
796:
791:
786:
781:
776:
771:
766:
764:Benzanthracene
760:
758:
754:
753:
751:
750:
745:
740:
735:
730:
728:Acenaphthylene
725:
719:
717:
713:
712:
710:
709:
704:
699:
693:
691:
687:
686:
681:
679:
678:
671:
664:
656:
648:
647:
620:
581:
554:
503:
475:
474:
472:
469:
468:
467:
461:
456:
451:
446:
439:
436:
435:
434:
411:
407:
393:
392:
373:
372:
356:
352:
313:
310:
309:
304:
282:
281:
277:standard state
274:
271:
270:
264:
258:
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163:DTXSID70209083
158:
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144:
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96:
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84:
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53:
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33:
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28:
27:
13:
10:
9:
6:
4:
3:
2:
1117:
1106:
1103:
1101:
1098:
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1091:
1088:
1087:
1085:
1070:
1067:
1065:
1062:
1060:
1057:
1055:
1052:
1050:
1047:
1046:
1044:
1040:
1034:
1031:
1029:
1026:
1024:
1021:
1019:
1016:
1014:
1011:
1009:
1006:
1004:
1001:
999:
996:
993:
989:
986:
984:
981:
979:
976:
974:
971:
969:
966:
965:
963:
959:
953:
950:
948:
945:
943:
940:
938:
935:
933:
930:
928:
927:Benzoperylene
925:
923:
920:
919:
917:
913:
907:
904:
902:
899:
897:
894:
892:
889:
887:
884:
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879:
877:
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872:
869:
867:
864:
862:
859:
857:
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850:
848:
843:
841:
838:
836:
833:
832:
831:
828:
826:
823:
822:
820:
816:
810:
807:
805:
802:
800:
797:
795:
792:
790:
787:
785:
782:
780:
777:
775:
774:Benzofluorene
772:
770:
769:Benzofluorene
767:
765:
762:
761:
759:
755:
749:
746:
744:
741:
739:
736:
734:
731:
729:
726:
724:
721:
720:
718:
714:
708:
705:
703:
700:
698:
695:
694:
692:
688:
684:
677:
672:
670:
665:
663:
658:
657:
654:
645:
641:
637:
633:
629:
624:
621:
618:
614:
610:
606:
602:
601:-butyllithium
600:
595:
591:
590:cycloaddition
585:
582:
579:
575:
571:
567:
563:
558:
555:
552:
548:
547:aromatization
544:
540:
536:
532:
528:
525:
521:
517:
513:
507:
504:
501:
497:
493:
489:
485:
480:
477:
470:
465:
462:
460:
457:
455:
452:
450:
447:
445:
442:
441:
437:
432:
428:
427:
426:
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421:
417:
405:
400:
398:
390:
386:
385:
384:
382:
378:
370:
366:
365:
364:
362:
349:
347:
343:
339:
335:
334:conformations
331:
327:
323:
319:
307:
300:
295:
278:
272:
265:
263:
260:
259:
244:
241:
237:
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231:
222:
218:
211:
197:
187:
183:
176:
168:
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159:
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147:
143:
142:
135:
131:
130:
128:
122:
118:
117:
110:
106:
105:
103:
101:
98:
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90:
86:
85:
83:
79:
74:
73:
66:
62:
61:
59:
56:
52:
51:
46:
38:
34:
29:
25:
20:
1105:Cyclobutenes
1100:Cyclobutanes
973:Dicoronylene
922:Anthanthrene
846:
808:
804:Triphenylene
789:Fluoranthene
748:Phenanthrene
723:Acenaphthene
635:
627:
623:
598:
584:
569:
561:
557:
541:followed by
518:followed by
506:
491:
483:
479:
459:Terthiophene
401:
394:
374:
359:) was first
350:
344:and form an
317:
316:
48:Identifiers
947:Triangulene
932:Corannulene
840:Benzopyrene
835:Benzopyrene
830:Benzopyrene
707:Naphthalene
592:between an
464:Naphthalene
454:Terpyridine
420:benzotriyne
377:bond length
361:synthesised
348:with them.
346:equilibrium
330:cyclobutane
233:Properties
1084:Categories
992:Hexa-cata-
733:Anthracene
527:hydrolysis
471:References
342:radialenes
262:Molar mass
100:ChemSpider
76:3D model (
65:60323-52-6
55:CAS Number
1069:Phenacene
1059:Cyclacene
1054:Circulene
983:Heptacene
891:Pentacene
799:Tetracene
743:Phenalene
607:group by
449:Triphenyl
1064:Helicene
1018:Sumanene
1008:Rubicene
998:Kekulene
968:Coronene
961:7+ rings
952:Zethrene
942:Hexacene
896:Perylene
784:Chrysene
738:Fluorene
697:Butalene
539:methanol
444:Biphenyl
438:See also
1033:Truxene
1013:Rubrene
1003:Ovalene
915:6 rings
818:5 rings
757:4 rings
716:3 rings
702:Azulene
690:2 rings
423:synthon
379:of 160
338:isomers
326:benzene
299:what is
297: (
267:156.228
121:PubChem
901:Picene
794:Pyrene
613:acetal
605:ketone
397:isatin
320:is an
294:verify
291:
217:SMILES
134:143698
109:126777
31:Names
1049:Acene
594:aryne
549:with
533:with
529:to di
524:ester
182:InChI
78:JSmol
636:2006
570:2006
545:and
492:1979
640:doi
574:doi
537:in
496:doi
340:of
151:EPA
124:CID
1086::
634:;
568:;
490:;
425:.
408:12
381:pm
357:12
353:12
255:12
249:12
994:)
990:(
847:H
845:6
675:e
668:t
661:v
642::
599:n
576::
498::
412:6
410:O
406:C
355:H
289:Y
252:H
246:C
153:)
149:(
80:)
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