ON THE REGIOSELECTIVITY OF THE NUCLEOPHILIC AROMATIC PHOTOSUBSTITUTION OF 4-NITROANISOLE. A DUAL MECHANISTIC PATHWAY

Article abstract of DOI:10.1016/S0040-4039(01)80417-2

4-Nitroanisole photoreacts with n-hexylamine and ethyl glycinate giving rise to regioselective methoxy and nitro group photosubstitutions respectively.Mechanistic evidences indicate the last is produced through a S_N2³Ar^* reaction whereas the first arises from a radical ion pair via electron transfer from the amine to a 4-nitroanisole triplet excited state.