Abstract
The direct and triplet-sensitized photochemistry of diphenylchloronium, diphenylbromonium, bis(4-methylphenyl) chloronium, and bis(4-methylphenyl) bromonium salts was studied. Direct photolysis of the diarylhalonium salts gave haloarene 2-, 3-, and 4-halobiaryls, and acetanilide, predominantly from a heterolytic cleavage mechanism via the aryl cation-haloarene pair, via in-cage recombination and cage-escape reactions. However, triplet-sensitized photolysis gave haloarene, 2-, 3-, and 4-halobiaryl, and reduced arene mainly from homolytic cleavage to the arene radical-haloarene radical cation pair, which also gave in-cage recombination and cage-escape products. There is evidence for singlet-triplet interconversion of the excited states by spin-orbit coupling and interconversion of the singlet-triplet radical pairs by spin-spin coupling. The effect of halogen and arene substituent on these interconversions is discussed
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