Tetrahedron letters

On the regioselectivity of the nucleophilic aromatic photosubstitution. The photoreaction of 4-nitroveratrole with n-hexylamine.

A Cantos, J Marquet, M Moreno-Mañas

Index: Cantos, Albert; Marquet, Jorge; Moreno-Manas, Marcial Tetrahedron Letters, 1987 , vol. 28, # 36 p. 4191 - 4194

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Citation Number: 13

Abstract

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.