NMR and X-ray crystallographic studies of linear and cyclic aminomethanephosphinates

Abstract

We report the preparation of four diastereoisomeric pairs of ethyl {[(3-hydroxypropyl)- amino](aryl)methyl}phenylphosphinates. In two cases, the phosphinates were transformed to 1,4,2-oxazaphosphepane heterocycles through one-pot intramolecular esterification. The analogous reaction with formaldehyde gave the six-membered ethyl (1,3-oxazinan-3-ylmethyl)phenylphosphinate, which could be transformed in a posterior reaction to the corresponding aminomethanephosphinic acid. The new compounds were characterized by IR, 1H, 13C, and 31P NMR. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:81–87, 2006; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20179