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Reaction of 3,4,3',4'-tetradehydrobiphenyl (bisbenzyne) with tetracyclone and acecyclone


Abstract:  3,4,3',4'-Tetradehydrobiphenyl 2 as a reactive intermediate was generated from aprotic diazotization reaction of 3,3'dicarboxy-4,4'-diaminobiphenyl 1 with isoamyl nitrite and subsequent thermal decomposition of the resulting diazonium salt. This intermediate is reacted with 2,3,4,5-tetraphenylcyclopentadienone (tetracyclone) 3 and 7,9-diphenyl-8H-cyclopenta[a]acenaphthylene-8-one (acecyclone) 6 and the resulting polycyclic aromatic hydrocarbons (PAH's) 4 and 9 are obtained in high yield.


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