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dc.contributor.authorAitken, Robert Alan
dc.contributor.authorKarodia, Nazira
dc.contributor.authorMcCarron, Hollie B
dc.contributor.authorRouxel, Cécile
dc.contributor.authorSahabo, Nina
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.identifier.citationAitken , R A , Karodia , N , McCarron , H B , Rouxel , C , Sahabo , N & Slawin , A M Z 2016 , ' Synthesis, structure and pyrolysis of stabilised phosphonium ylides containing saturated oxygen heterocycles ' , Organic & Biomolecular Chemistry , vol. 14 , no. 5 , pp. 1794-1804 .
dc.identifier.otherPURE: 240105150
dc.identifier.otherPURE UUID: 8d964b50-19ee-4319-a50c-fb692210f7bd
dc.identifier.otherScopus: 84956994640
dc.identifier.otherORCID: /0000-0001-6959-5311/work/34857573
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56862092
dc.identifier.otherWOS: 000369600000036
dc.description.abstractA range of twelve stabilised phosphonium ylides containing tetrahydrofuran, tetrahydropyran or 2,2-dimethyl-1,3-dioxolane rings have been prepared and fully characterised, including one X-ray structure determination of each type. The X-ray structures confirm the P=C and C=O functions to be syn and all the compounds undergo thermal extrusion of Ph3PO to give the corresponding alkynes. In some cases there is also competing loss of Ph3P to give different carbene-derived products and evidence has been obtained for the generation of 2-phenyloxete in this way. Raising the pyrolysis temperature leads in several cases to new secondary reactions of the alkyne products involving a sequence of alkyne to vinylidene isomerisation, intramolecular CH insertion, and retro Diels Alder reaction.
dc.relation.ispartofOrganic & Biomolecular Chemistryen
dc.rightsCopyright 2015 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (
dc.subjectQD Chemistryen
dc.titleSynthesis, structure and pyrolysis of stabilised phosphonium ylides containing saturated oxygen heterocyclesen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.description.statusPeer revieweden

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