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Kinetic and structure-activity studies of the triazolium Ion-catalyzed intramolecular stetter reaction
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dc.contributor.author | Collett, Christopher John | |
dc.contributor.author | Young, Claire Mary | |
dc.contributor.author | Massey, Richard. S. | |
dc.contributor.author | O'Donoghue, AnnMarie | |
dc.contributor.author | Smith, Andrew David | |
dc.date.accessioned | 2021-06-01T11:30:15Z | |
dc.date.available | 2021-06-01T11:30:15Z | |
dc.date.issued | 2021-07-15 | |
dc.identifier | 274078833 | |
dc.identifier | 15ce3595-a7b5-4b7a-8692-96e6468dd2ad | |
dc.identifier | 000656362300001 | |
dc.identifier | 85107404415 | |
dc.identifier.citation | Collett , 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.202100384 | en |
dc.identifier.issn | 1434-193X | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/95041690 | |
dc.identifier.uri | https://hdl.handle.net/10023/23293 | |
dc.description | Funding: Engineering and Physical Sciences Research Council (Grant Number(s): EP/E03795X/1, EP/S019359/1). | en |
dc.description.abstract | Mechanistic 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.extent | 7 | |
dc.format.extent | 2385362 | |
dc.language.iso | eng | |
dc.relation.ispartof | European Journal of Organic Chemistry | en |
dc.subject | NHC | en |
dc.subject | Breslow intermediate | en |
dc.subject | Triazolium | en |
dc.subject | Stetter reaction | en |
dc.subject | Initial rates analysis | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Kinetic and structure-activity studies of the triazolium Ion-catalyzed intramolecular stetter reaction | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | https://doi.org/10.1002/ejoc.202100384 | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | EP/S019359 | en |
dc.identifier.grantnumber | EP/E03795X/1 | en |
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