REACTION OF PHENCYCLONE WITH ARYNE AND BISARYNE

Benzyne (2a) and 4-chlorobenzyne (2b) from the corresponding anthranil ic acids have been reacted with 1,3-diphenyl-2 H-cyclopent[b]phenanthr en-2-one (3) (phencyclone) at different temperature. In boiling 1,2-di chloroethane, a mixture of carbonyl-bridged adduct (4) and decarbonyla ted product (5) is formed. But in methylene chloride only carbonyl-bri dged adduct (4) is formed in quantitative yield. In boiling 1,1,2,2-te trachloroethane, however, the decarbonylated adduct (5) is formed in h igh yield. Bisbenzyne (6) from aprotic diazotization of 3,3'-dicarboxy l-4,4'-diaminobiphenyl is also reacted with this cyclone leading to th e formation of a novel polyaromatic adduct 14'-tetraphenyl-11,11'-bis( dibenzo[a,c]anthracene) (8) in good yield.