Reaction of thiolo and selenolo esters of phosphorus acids with halogens. Part 3. Interaction of O, O,S-trialkyl phosphorothioates and O,S-dialkyl t-butylphosphonothioates with sulphuryl chloride and halogens

Abstract

The reaction of the title phosphon- and phosphoro-thiolates with sulphuryl chloride and halogens involves in every case the formation of intermediates containing two phosphorus atoms > P(SR)OP(O) < X–(X = SO2Cl or halogen). The formation of the latter in the course of chlorinolysis of phosphorus thiolesters is suggested to be responsible for the occurrence of a mechanism involving retention of configuration. The effect of the structure of the reactants and the nature of solvent on the reaction stereochemistry is discussed.