Dicyanobenzene sensitized carbon-carbon bond cleavage in methoxybicumenes. Products and mechanistic studies

Article abstract of DOI:10.1016/S0040-4020(01)88366-6

Radical cations of p-methoxy-p-X-bicumenes generated by ET to excited-state dicyanobenzene undergo rapid irreversible C-C bond scission giving cumyl cations and radicals. The photoefficiency of the process (Φ = 0.13 for X = MeO, Φ< 0.005 for X = CN) and the fate of the radicals produced depends strongly on substitution.