Reactions of arylcyclohexadienyl radicals: rearrangement versus fragmentation

Abstract

The genesis of 1-chloro-6-phenylcyclohexadienyl radicals and of 6,6-diphenylcyclohexadienyl radicals is described. The reactions of neither radical have given any evidence for intramolecular aryl migration. A major high-temperature reaction of the 6,6-diphenylcyclohexadienyl radical is fragmentation, giving phenyl radicals and biphenyl. Evidence for fragmentation of 6-phenylcyclohexadienyl radicals at ca. 200° has also been found.