Phosphonamidothioic acids as thiophosphonylating agents: stereochemistry of reactions of N-tert-butyl-P-phenylphosphonamidothioic acid with alcohols
Abstract
Enantiopure PhP(S)(OH)NHBut reacts with alcohols in CH2Cl2 to give PhP(S)(OH)OR (R = Me, Pri, But); reaction is completely non-stereospecific with ButOH and largely so with PriOH and very low concentrations of MeOH, pointing to the involvement of a thiometaphosphonate (PhPOS) intermediate.