THE ACIDIC CLEAVAGE OF PYRIDYLMETHYL(AMINO)PHOSPHONATES - FORMATION OF THE CORRESPONDING AMINES

Hydrolysis of 3-pyridylmethyl(amino)phosphonates by means of 20% aq. h ydrochloric acid gave corresponding 3-pyridylmethyl(amino)phosphonic a cids, as expected However, hydrolysis of 2- and 4-pyridylmethyl(amino) phosphonates led to decomposition of the phosphonates with a cleavage of C-P bond and formation of the corresponding amines. The leaving pho sphorus moiety was identified as phosphoric acid. The scope of the rea ction is limited to 2- and 4-pyridylmethyl derivatives of aminophospho nic acids and their esters, as well as to the derivatives possessing s imilar structure. In the contrary, the basic hydrolysis of 2- and 4-py ridylmethyl(amino)phosphonates led to the corresponding monoalkyl este rs of the aminophosphonates, and no a cleavage of C-P bond was observe d in those cases. Copyright (C) 1996 Elsevier Science Ltd