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

被引：39

作者：

Byrne, Peter A. ^{[1
]}

Ortin, Yannick ^{[1
]}

Gilheany, Declan G. ^{[1
]}

机构：

[1] Univ Coll Dublin, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 06期

基金：

爱尔兰科学基金会;

关键词：

NUCLEAR-MAGNETIC-RESONANCE; P-31; NMR-SPECTROSCOPY; WITTIG REACTION; ALKALINE-HYDROLYSIS; PHOSPHINE OXIDES; HETEROARYLPHOSPHORUS COMPOUNDS; TOPOLOGICAL REPRESENTATION; NUCLEOPHILIC DISPLACEMENT; SUBSTITUTION REACTIONS; EQUILIBRIUM ACIDITIES;

D O I：

10.1039/c4cc08644a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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-hydroxy-tetraorganophosphorane is generated directly by 4-centre reaction of ylide with water.

引用

页码：1147 / 1150

页数：4

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