On the regioselectivity of the nucleophilic aromatic photosubstitution. The photoreaction of 4-nitroveratrole with n-hexylamine.
1987; Elsevier BV; Volume: 28; Issue: 36 Linguagem: Inglês
10.1016/s0040-4039(00)95576-x
ISSN1873-3581
AutoresAlbert Cantos, Jordi Marquet, Marcial Moreno‐Mañas,
Tópico(s)DNA and Nucleic Acid Chemistry
Resumo4-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.
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