Abstract 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 SN 2 Ar 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.
