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Issue 6, 2015
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First ever observation of the intermediate of phosphonium salt and ylide hydrolysis: P-hydroxytetraorganophosphorane

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Abstract

P-Hydroxytetraorganophosphorane, the long-postulated intermediate in phosphonium salt and ylide hydrolysis, has been observed and characterised by low temperature NMR, finally definitively establishing its involvement in these reactions. The results require modification of the previously accepted mechanism for ylide hydrolysis: P-hydroxytetraorganophosphorane is generated directly by 4-centre reaction of ylide with water.

Graphical abstract: First ever observation of the intermediate of phosphonium salt and ylide hydrolysis: P-hydroxytetraorganophosphorane

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Supplementary files

Article information


Submitted
31 Oct 2014
Accepted
23 Nov 2014
First published
26 Nov 2014

Chem. Commun., 2015,51, 1147-1150
Article type
Communication
Author version available

First ever observation of the intermediate of phosphonium salt and ylide hydrolysis: P-hydroxytetraorganophosphorane

P. A. Byrne, Y. Ortin and D. G. Gilheany, Chem. Commun., 2015, 51, 1147
DOI: 10.1039/C4CC08644A

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