o-Phthalaldehyde catalyzed hydrolysis of organophosphinic amides and other P(=O)-NH containing compounds
Over 50 years ago, Jencks and Gilchrist showed that formaldehyde catalyses the hydrolysis of phosphoramidate through electrophilic activation, induced by covalent attachment to its nitrogen atom. Given our interest in the use of aldehydes as catalysts, this work was revisited to identify a superior...
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Published in | Chemical communications (Cambridge, England) Vol. 53; no. 62; pp. 8667 - 8670 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
CAMBRIDGE
Royal Soc Chemistry
11.08.2017
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Subjects | |
Online Access | Get full text |
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Summary: | Over 50 years ago, Jencks and Gilchrist showed that formaldehyde catalyses the hydrolysis of phosphoramidate through electrophilic activation, induced by covalent attachment to its nitrogen atom. Given our interest in the use of aldehydes as catalysts, this work was revisited to identify a superior catalyst, o-phthalaldehyde, which facilitates hydrolyses of various organophosphorus compounds bearing P(=O)-NH subunits under mild conditions. Interestingly, chemoselective hydrolysis of the P(=O)-N bonds could be accomplished in the presence of P(=O)-OR bonds. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1359-7345 1364-548X |
DOI: | 10.1039/c7cc04950a |