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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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Publication details

The article was received on 31 Oct 2014, accepted on 23 Nov 2014 and first published on 26 Nov 2014


Article type: Communication
DOI: 10.1039/C4CC08644A
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Chem. Commun., 2015,51, 1147-1150

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    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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