Influence of ion pairing, steric effects, and other specific interactions on the reactivity of thioanions with chloronitrobenzenes. Nucleophilic aromatic substitution vs. …

S Montanari, C Paradisi, G Scorrano

Index: Montanari, Stefano; Paradisi, Cristina; Scorrano, Gianfranco Journal of Organic Chemistry, 1991 , vol. 56, # 13 p. 4274 - 4279

Full Text: HTML

Citation Number: 26

Abstract

The reactions in 2-propanol of the ieomeric chloronitrobenzenes with thiolate nucleophiles, RS-(R= Me, i-Pr, t-Bu, Ph), have been studied to teat for the ability of these representative thioanions of inducing chloride displacement and/or nitro reduction. m-Chloronitrobenzene gives a complex mixture of products, all still retaining the chlorine substituent, via redox processes involving nitro reduction and ring alkylthiolation. In contrast, the ortho and para ...