Open AccessThe selective phosphylation of ethanolamine
Author(s) -
R. Greenhalgh,
Martin Weinberger
Publication year - 1967
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v67-084
Subject(s) - chemistry , ethanolamine , moiety , pyrophosphate , organic chemistry , ethanolamines , medicinal chemistry , enzyme
In nonaqueous solvents under conditions where phosphylation of either of the functional groups of ethanolamine can occur, it is found that phosphofluoridates react exclusively with the hydroxyl group. This O-phosphylation appears to be specific for phosphofluoridates, since phosphochloridates, tetraethyl pyrophosphate, and ethyl N,N-dimethylphosphoramidocyanidate react predominantly with the amino moiety. However, with these compounds the reaction is not as specific, some O-phosphylation being observed, especially with the last compound. Possible reasons for this difference in behavior are discussed.