First ever observation of the intermediate of phosphonium salt and ylide hydrolysis: P-hydroxytetraorganophosphorane. Issue 6 (3rd December 2014)

• Record Type: Journal Article
• Authors: Byrne, Peter A.; Ortin, Yannick; G. Gilheany, Declan
• Is Part Of: Chemical communications. Volume 51:Issue 6(2015)
• Page Start: 1147
• Page End: 1150
• Publication Date: 2014-12-03
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c4cc08644a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : P -Hydroxytetraorganophosphorane, the putative intermediate in phosphonium salt & ylide hydrolysis reactions, has been observed and characterised for the first time, thus establishing unequivocally its existence & involvement in these reactions. 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.