Displacements on phosphoramidates: the nature of the transition state

Abstract

The preparation and reactions of some monoesterified phosphoramidic acids derived from N-phenylethylenediamine and 2-aminobenzylamine, in which the phosphoryl group is attached to the more strongly basic amino-group, are reported. The failure to detect intramolecular attack by the vicinal amino-group is discussed in relation to the steric requirements of the transition state of nucleophilic displacements on phosphorus.