Synthesis of aminophosphonates with a primary amino group

Mono- and dinitro-substituted aromatic Shiff bases were reacted with diisop ropyl hydrogen phosphite in the presence of the boron trifluoride-ether com plex to obtain the corresponding alpha-aminophosphonates. Reduction of the nitro groups in the resulting phosphonates with iron in the presence of ace tic acid in aqueous toluene gave diisopropyl (arylamino)arylmetylphosphonat es with one or two primary amino groups at the aromatic substituents. The s tructure of the products was studied by H-1 NMR and IR spectroscopy.