Synthetic utilization of polynitroaromatic compounds. 1. S-derivatization of 1-substituted 2, 4, 6-trinitrobenzenes with thiols

…, V Samet, A Serebryakov, D Konyushkin…

Index: Zlotin; Kislitsin; Samet; Serebryakov; Konyushkin; Semenov; Buchanan III; Gakh Journal of Organic Chemistry, 2000 , vol. 65, # 25 p. 8430 - 8438

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Citation Number: 37

Abstract

Reactions of 1-R-2, 4, 6-trinitrobenenes (R= alkyl, protected aldehyde, aminocarbonyl, cyano groups, or isoxazole ring) with thiol salts were investigated. In most cases, these reactions gave a mixture of minor para and major ortho substitution products. Reactions of N, N-disubstituted 2, 4, 6-trinitrobenzamides with S-, O-, and N-nucleophiles afforded products of substitution of the p-nitro group exclusively. 1-Cyano-2, 4, 6-trinitrobenzene ...