Nucleophilic substitution in α-halogeno-sulphoxides. Part II. Dependence of the reaction mechanism on structural factors and on the nature of nucleophile

Abstract

Nucleophilic substitutions on α-halogeno-sulphoxides proceed through two competitive mechanisms, a direct S₅2 substitution and an elimination–addition process. The prevalence of either of the paths depends on the structure of the substrate and on the nature of the nucleophile. S_N2 Displacement occurs in the reaction of α-halogenoethyl sulphoxides with EtS^–, while elimination-addition takes place in the reaction of these substrates with PrⁿO^– and in the reaction of 1-halogeno-1-methylethyl derivatives with both nucleophiles.