A series of four diethyl {[(3-hydroxy-propyl)amino](aryl)methyl}phosphonates have been prepared and characterized. In one case, the phosphonate was transformed to a seven-membered 1,4,2-oxazaphosphepane heterocycle through a one-pot intramolecular esterification. The analogous reaction with formaldehyde gave the six-membered diethyl (1,3-oxazinan-3-ylmethyl)phosphonate, which could be transformed in a posterior reaction to the corresponding aminomethanephosphonic acid.

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Organo-phosphorus compounds S 0080Linear and Cyclic Aminomethanephosphonic Acid Esters Derived from Benzaldehyde Derivatives, 3-Aminopropanol, and Diethyl Phosphite. -Hydrophosphonylation reactions of aminopropanol (I) with benzaldehydes (II) yield phosphonates (IV) which are characterized by the presence of an intramolecular hydrogen bond. Benzaldehydes possessing electron-donating groups also generate oxazaphosphepane heterocycles via an intramolecular esterification, cf. (VII). An analogous reaction with formaldehyde (VIII) affords the oxazinanylmethyl phosphonate (IX), which can be hydrolyzed to the phosphonic acid (X). -(ZAMORANO-OCTAVIANO, J.; HERNANDEZ-MARTINEZ, A.; ORTEGA-GUEVARA, A.; LINZAGA-ELIZALDE*, I.; HOEPFL, H.; Heteroat. Chem. 17 (2006) 2, 75-80; Cent. Invest. Quim., Univ. Auton. Estado Morelos, 62210 Cuernavaca, Mex.; Eng.) -H. Hoennerscheid 31-158