Associative vs. dissociative mechanism of P-C bond breaking in α-aminophosphonates leading to phosphoric acid [P(V)] derivatives.

Abstract

The α-aminophosphonates are relatively easily protonated on phosphoryl oxygen in acidic conditions due the neighboring amine group effect. Protonation of phosphoryl oxygen makes the phosphorus atom highly electrophilic and suitable for decomposition with P-C bond breaking to P III or P V decomposition products.