Author :
Mallakpour, shadpour E.,Karami-Dezcho, bahador
Descriptors :
Benzyne,Bis-benzyne,Cycloaddition reaction,Reactive intermediate
Abstract :
Benzyne (2a) and 4-chlorobenzyne (2b) from the corresponding anthranilic acide have been reacted with 1,3-diphenyl-2H-cyclopent[b]phenanthren-2-one (3) (phencyclone) at different temperature. In boiling 1,2-dichloroethane, a mixture of carbonyl-bridged adduct (4) and decarbonylated product (5) is formed. But in methylene chloride only carbonyl-bridged adduct (4) is formed in quantitative yield. In boiling 1,1,2,2-tetrachloroethane, however, the decarbonylated adduct (5) is formed in high yield. Bisbenzyne (6) from aprotic diazotization of 3,3ʹ-dicarboxyl-4,4ʹ-diaminobiphenyl is also reacted with this cyclone leading to the formation of a novel polyaromatic adduct 9,14,9ʹ,14ʹ-tetraphenyl-11,11ʹ-bis(dibenzo[a,c]anthracene)(8) in food yield.
