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

Albert Cantos, Jorge Marquet, Marcial Moreno-Mañas

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11 Citations (Scopus)

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 SN2Ar 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. © 1987.
Original languageEnglish
Pages (from-to)4191-4194
JournalTetrahedron Letters
Volume28
Issue number36
DOIs
Publication statusPublished - 1 Jan 1987

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