Peer-Reviewed Journal Details
Mandatory Fields
Byrne, PA;Ortin, Y;Gilheany, DG
2015
January
Chemical Communications
First ever observation of the intermediate of phosphonium salt and ylide hydrolysis: P-hydroxytetraorganophosphorane
Validated
WOS: 8 ()
Optional Fields
NUCLEAR-MAGNETIC-RESONANCE P-31 NMR-SPECTROSCOPY WITTIG REACTION ALKALINE-HYDROLYSIS PHOSPHINE OXIDES HETEROARYLPHOSPHORUS COMPOUNDS TOPOLOGICAL REPRESENTATION NUCLEOPHILIC DISPLACEMENT SUBSTITUTION REACTIONS EQUILIBRIUM ACIDITIES
51
1147
1150
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.
CAMBRIDGE
1359-7345
10.1039/c4cc08644a
Grant Details