Author :
Mallakpour, S. E.,Williamson, J. R
Title of Article :
Synthesis and trapping of 3,4,3 ,4ʹ-thetradehyorobiphenyl (Bisbenzyne)
Descriptors :
Benzyne,Bisbenzyne,Diels-Alder reaction,Cycloaddition reaction,Reactive intermediate
Abstract :
3,3ʹ-Dicarboxy-4,4ʹ-diaminobiphenyl was synthesized from onitrobenzoic acid following standard procedures. Diazotization of thid compound with isoamylnitrite, under aprotic condition gave diphenyl-4,4ʹ-bis-diazonium-s,sʹ-dicarboxylate and subsequent thermal decomposition of this diazonium compound produced 3,4,3ʹ,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 5,6,7,5ʹ,6ʹ,7ʹ,8ʹ, octaphenyl-2,2ʹ-binaphthyl. This novel compound was fully characterized by elemental analysis IR and 1HNMR spectroscopy.
