The structure and reactivity of N-Acyl phosphoric amides and related systems
Two synthetic approaches towards the N-acyl phosphylamide system Z₂P(O)-NR-C(O)R' (1; Z =alkyl, O-alkyl; R = H, Me; R' =M e, Ph), from phosphylamide and carboxamide precursors are discussed. The infrared, ¹H and ¹³C NMR spectral features of system (1), indicate predominant resonance interaction of the nitrogen non-bonding electrons with the adjacent carboxyacyl, rather than phosphacyl centre. The electron-with- drawing effect of the phosphyl substituent Z₂P(O), is nonetheless sub- stantial, thus weakening the basicity and nucleophilicity of the nitrogen atom and enhancing the electrophilicity of the carbonyl centre. The influence of the electronic distribution within the OPNCO moiety upon the structure and reactivity of (1), has been investigated.
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