The lack of influence of electronic effects on the stereochemistry of the oxidation of aryl thiophosphates

Abstract

A series of epimeric six-membered cyclic aryl thiophosphates 1–7 were oxidized to their corresponding phosphates by means of a mixture of aqueous hydrogen peroxide (30%) and hydrogen chloride. The oxidation, under these conditions, is highly stereospecific so that the products were obtained in quantitative yields with retention of configuration at the phosphorus center. Our results do not support the participation of pentacoordinate species as plausible intermediates of the oxidation reaction.