Tetrahedron

Tele-versus normal substitution in the reaction of 1, 4-dialkyl-2, 3-dinitronaphthalenes with sodium arenethiolates in dmso

M Novi, G Guanti, S Thea, F Sancassan, D Calabro

Index: Novi,M. et al. Tetrahedron, 1979 , vol. 35, p. 1783 - 1788

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Citation Number: 12

Abstract

1, 4-Dimethyl-2, 3-dinitronaphthalene (1) reacts with sodium arenethiolates in DMSO to give 2-arylthio-1, 4-dimethyl-3-nitronaphthalene (3)[normal substitution product (NSP)] and 1- arylthiomethyl-4-methyl-3-nitronaphthalene (5)[tele-substitution product (TSP)]. The percentage of TSP is found to increase with the enhancement of the reaction temperature, the presence of electron-withdrawing substituents in the arenethiolate; the increase of ...