ON THE REGIOSELECTIVITY OF THE NUCLEOPHILIC AROMATIC PHOTOSUBSTITUTION. THE PHOTOREACTION OF 4-NITROVERATROLE WITH n-HEXYLAMINE.

Article abstract of DOI:10.1016/S0040-4039(00)95576-X

4-Nitroveratrole is photosubstituted with n-hexylamine giving rise to two isomeric anilines, N-hexyl-2-methoxy-5-nitroaniline and N-hexyl-2-methoxy-4-nitroaniline.Mechanistic evidence indicates that the first is produced in an S_N2Ar* reaction through singlet and triplet excited states, whereas the second arises from a radical ion pair via electron transfer from the amine to a triplet excited state.