THE REARRANGEMENT OF 4,4-DIPHENYLCYCLOHEXA-2,5-DIENYLIDENE

Article abstract of DOI:10.1016/0040-4020(82)80085-9

Pyrolytic decomposition of the Li salt of the tosylhydrazone of 4,4-diphenyl-2,5-cyclohexadienone produces a mixture of biphenyl, o-terphenyl, p-terphenyl, methyl-o-terphenyl and the azine of 4,4-diphenyl-2,5-cyclohexadienone (13).Insight into the reaction pathway was provided by the pyrolytic decomposition of 2-deuterio tosylhydrazone 8a which generates o-terphenyl 10a and 10b in a ratio of 69:31.These results are interpreted in terms of the carbene rearrangements of Schemes 2, 3 and 5.