Phase-transfer mechanism and nucleophilicity of halide ions in an aqueous–organic two-phase system

Abstract

Nucleophilic substitution by halide ions in n-octyl methanesulphonate catalysed by hexadecyltri-butylphosphonium halides in a water–chlorobenzene two-phase system occurs in the organic phase; the reactivity range (Cl^–:Br^–:I^–= 0·6:1·1:1) is largely determined by the specific solvation of the anion by a limited number of water molecules.