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

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dc.contributor.authorByrne, Peter A.
dc.contributor.authorOrtin, Yannick
dc.contributor.authorGilheany, Declan G.
dc.contributor.funderScience Foundation Irelanden
dc.date.accessioned2019-04-04T11:25:51Z
dc.date.available2019-04-04T11:25:51Z
dc.date.issued2014-11-26
dc.date.updated2019-03-26T17:42:42Z
dc.description.abstractP-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.en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationByrne, P. A., Ortin, Y. and G. Gilheany, D. (2015) 'First ever observation of the intermediate of phosphonium salt and ylide hydrolysis: P-hydroxytetraorganophosphorane', Chemical Communications, 51(6), pp. 1147-1150. doi: 10.1039/c4cc08644aen
dc.identifier.doi10.1039/c4cc08644aen
dc.identifier.eissn1364-548X
dc.identifier.endpage1150en
dc.identifier.issn1359-7345
dc.identifier.journaltitleChemical Communicationsen
dc.identifier.startpage1147en
dc.identifier.urihttps://hdl.handle.net/10468/7708
dc.identifier.volume51en
dc.language.isoenen
dc.publisherRoyal Society of Chemistry (RSC)en
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/en
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Infrastructure Programme/12/RI/2341 (2)/IE/Advanced materials/surface characterization system including XPS/AES/SIMS/en
dc.relation.urihttps://pubs.rsc.org/en/Content/ArticleLanding/2015/CC/C4CC08644A
dc.rights© The Royal Society of Chemistry 2015en
dc.subjectNuclear magnetic resonanceen
dc.subjectP-31 NMR spectroscopyen
dc.subjectWittig reactionen
dc.subjectAlkaline hydrolysisen
dc.subjectPhosphine oxidesen
dc.subjectHeteroarylphosphorus compoundsen
dc.subjectTopological representationen
dc.subjectNucleophilic displacementen
dc.subjectSubstitution reactionsen
dc.subjectEquilibrium aciditiesen
dc.titleFirst ever observation of the intermediate of phosphonium salt and ylide hydrolysis: P-hydroxytetraorganophosphoraneen
dc.typeArticle (peer-reviewed)en
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