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

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 carba...

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Published inHeteroatom chemistry Vol. 19; no. 2; pp. 119 - 124
Main Authors Troev, K., Koseva, N., Hägele, G.
Format Journal Article
LanguageEnglish
Published Hoboken Wiley Subscription Services, Inc., A Wiley Company 01.03.2008
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Abstract 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
AbstractList Abstract 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 1 H, 13 C, 31 P 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
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
Author Koseva, N.
Hägele, G.
Troev, K.
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Snippet 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...
Abstract It was found that the reaction of dimethyl H‐phosphonate ( 1 ) with 2‐hydroxyalkyl‐ N ‐2′‐hydroxyalkyl carbamates at 135°C includes several chemical...
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Title Novel routes to aminophosphonic acids: Interaction of dimethyl H-phosphonate with hydroxyalkyl carbamates
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