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

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

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 me...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2015-01, Vol.51 (6), p.1147-1150
Hauptverfasser: Byrne, Peter A, Ortin, Yannick, Gilheany, Declan G
Format: Artikel
Sprache:eng
Schlagworte:
Hydrolysis
Nuclear magnetic resonance
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Zusammenfassung: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc08644a