Tetraorganylphosphonium chloride and arenesulfonates

Abstract

The interaction of equimolar amounts of triphenylphosphorus dichloride with penta-phenylphosphorus in benzene have synthesized tetraphenylphosphonium chloride (1), which reacts with arenesulfonic acids to form tetraphenylphosphonium arenesulfonates [Ph4P][OSO2C6H3(OH-4)(COOH-3]∙H2O (2), [Ph4P][OSO2C10H5(OH-1)(NO2)2-2,4] (3), yielding up to 82%. A similar reaction of cyclohexyltriphenylphosphonium chloride with 2-sulfobenzoic acid is accompanied by the synthesis of cyclohexyltriphenylphosphonium 2-carboxybenzenesulfonate [Ph3P(С6H11-cyclo)][OSO2C6H4(COOH-2)] (4), yielding 80%. Structural features of complexes 24 have been established by X-ray diffraction. It has been shown that in cations 2–4 the phosphorus atoms have a distorted tetrahedral coordination, and for arenesulfonate anions the usual geometry with a tetrahedral sulfur atom is observed.