%0 Journal Article %T Synthesis and Trapping of 3,4,3',4'-Tetradehydrobiphenyl (Bisbenzyne) %J Iranian Journal of Chemistry and Chemical Engineering %I Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR %Z 1021-9986 %A Williamson, J.R. %A Mallakpour, Shadpour %D 1991 %\ 06/01/1991 %V 10 %N 1 %P 66-78 %! Synthesis and Trapping of 3,4,3',4'-Tetradehydrobiphenyl (Bisbenzyne) %K Synthesis %K Trapping %K 3 %K 4 %K 3' %K 4'-Tetradehydrobiphenyl (Bisbenzyne) %R 10.30492/ijcce.1991.10951 %X 3,3'-Dicarboxy-4,4'-diaminobiphenyl was synthesized from Onitrobenzoic acid following standard procedures. Diazotization of this compound with isoamylnitrite, under approtic condition gave diphenyl-4,4'-bis-diazonium-3,3'-dicarboxylate and subsequent thermal decomposition of this diazonium compound produced 3,4,3',4'-tetradehydrobiphenyl (bisbenzyne) as a reactive intermediate. Bisbenzyne was trapped with the diene 2,3,4,5-tetraphenylcyclopentadienone via a [4+2]diels-Alder cycloaddition reaction yielding the previously unreported 5,6,7,8,5',6',7',8'-octaphenyl-2,2'-binaphthyl. This novel compound was fully characterized by elemental analysis IR and 1HNMR spectroscopy. %U https://ijcce.ac.ir/article_10951_aa1a11368d2f7a52b8198f80a47867fa.pdf