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dc.contributor.authorCollett, Christopher John
dc.contributor.authorYoung, Claire Mary
dc.contributor.authorMassey, Richard. S.
dc.contributor.authorO'Donoghue, AnnMarie
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2021-06-01T11:30:15Z
dc.date.available2021-06-01T11:30:15Z
dc.date.issued2021-07-15
dc.identifier.citationCollett , C J , Young , C M , Massey , R S , O'Donoghue , A & Smith , A D 2021 , ' Kinetic and structure-activity studies of the triazolium Ion-catalyzed intramolecular stetter reaction ' , European Journal of Organic Chemistry , vol. 2021 , no. 26 , 202100384 , pp. 3670-3675 . https://doi.org/10.1002/ejoc.202100384en
dc.identifier.issn1434-193X
dc.identifier.otherPURE: 274078833
dc.identifier.otherPURE UUID: 15ce3595-a7b5-4b7a-8692-96e6468dd2ad
dc.identifier.otherORCID: /0000-0002-2104-7313/work/95041690
dc.identifier.otherWOS: 000656362300001
dc.identifier.otherScopus: 85107404415
dc.identifier.urihttp://hdl.handle.net/10023/23293
dc.descriptionFunding: Engineering and Physical Sciences Research Council (Grant Number(s): EP/E03795X/1, EP/S019359/1).en
dc.description.abstractMechanistic studies of the triazolium ion‐catalyzed intramolecular Stetter reaction using initial rates analysis in NEt3/NEt3. HCl buffered methanol showed the reaction to be first order in catalyst and zero order in aldehyde over a broad range of aldehyde concentrations. The observed reaction rate is higher for catalysts bearing N‐aryl substituents with electron‐withdrawing groups. A concurrent, NHC‐independent substrate isomerization was also observed and found to demonstrate a first order dependence on aldehyde concentration. The reported data are consistent with deprotonation to form the Breslow intermediate being turnover‐limiting in this process.
dc.format.extent7
dc.language.isoeng
dc.relation.ispartofEuropean Journal of Organic Chemistryen
dc.rightsCopyright © 2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.en
dc.subjectNHCen
dc.subjectBreslow intermediateen
dc.subjectTriazoliumen
dc.subjectStetter reactionen
dc.subjectInitial rates analysisen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleKinetic and structure-activity studies of the triazolium Ion-catalyzed intramolecular stetter reactionen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.identifier.doihttps://doi.org/10.1002/ejoc.202100384
dc.description.statusPeer revieweden


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