Novel routes to aminophosphonic acids: Interaction of dimethyl H-phosphonate with hydroxyalkyl carbamates

• Published in: Heteroatom chemistry Vol. 19; no. 2; pp. 119 - 124
• Main Authors: Troev, K., Koseva, N., Hägele, G.
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley Subscription Services, Inc., A Wiley Company 01.03.2008
• ISSN: 1042-7163; 1098-1071
• DOI: 10.1002/hc.20404

It was found that the reaction of dimethyl H‐phosphonate (1) with 2‐hydroxyalkyl‐N‐2′‐hydroxyalkyl carbamates at 135°C includes several chemical reaction steps: (i) chemical transformations of 1‐methyl‐2‐hydroxyethyl‐N‐2′‐hydroxyethyl carbamate (2) and 2‐methyl‐2‐hydroxyethyl‐N‐2′‐hydroxyethyl carbamate (3); (ii) transesterification of dimethyl H‐phosphonate with 2 and 3, and with secondary hydroxyl‐containing compounds that are formed during the course of the chemical transformation of 2‐hydroxyalkyl‐N‐2′‐hydroxyalkyl carbamates; (iii) hydrolysis of 1 and dialkyl H‐phosphonates, formed via transesterification of 1 with secondary hydroxyl‐containing compounds. The interaction was studied by means of 1H, 13C, 31P NMR, and FAB mass spectroscopy. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:119–124, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20404