Radical–nucleophilic substitution (SRN1) reactions. Part 2. Preparation and reactions of α-nitrosulphides

Abstract

A range of α-nitrosulphides [Me₂C(SR)NO₂, with R = 2-pyridyl, pyrimidin-2-yl, 1,3-benzothiazol-2-yl, 1-methylimidazol-2-yl, and 4,5-dihydro-1,3-thiazol-2-yl] have been prepared by oxidative addition of thiolate anion to the anion of 2-nitropropane, S_N2 attack of the anion of 2-nitropropane on symmetrical disulphides, and S_RN1 reaction of 2-substituted-2-nitropropanes with thiolate anions. The α-nitrosulphides undergo S_RN1 substitution with the anion of 2-nitropropane, and S_RN1 substitution or redox reactions with thiolate anions. The electron spin resonance (e.s.r.) spectrum of the radical-anion of 1-methyl-1-nitroethyl pyrimidin-2-yl sulphide has been observed.