Protonation and Phosphorus-Oxygen Cleavage of Phosphorus(III) Esters by Hydrogen Chloride

Abstract

The formation of alkyl chlorides in the reactions of alcohols with phosphorus trichloride, dichlorophenylphosphine, or chlorodiphenylphosphine involves the dealkylation of an intermediate phosphorus(III) ester by hydrogen chloride (Scheme 1).^1–3 An analogous dealkylation occurs in the reactions of hydrogen chloride with triphenyl phosphite-alcohol mixtures (Scheme 2).⁴