Kinetic isotope effects of nitrogen and hydrogen in reaction of N-tert-butyl-P-phenylphosphonamidothioic acid with alcohols

The intermediacy of metathiophosphonate PhPSO in the reaction of N-tert-butyl-P-phenylphosphonamidothioic acid with alcohols (MeOH, BuOH, PriOH, ButOH) is proposed on the basis of nitrogen and hydrogen kinetic isotope effects, as well as semiempirical PM3 calculations. For the reaction with methanol the alternative addition-elimination mechanism cannot be excluded.