Files in this item
Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions : role of the N-aryl substituent
Item metadata
dc.contributor.author | Collett, Christopher J. | |
dc.contributor.author | Massey, Richard S. | |
dc.contributor.author | Maguire, Oliver R. | |
dc.contributor.author | Batsanov, Andrei S. | |
dc.contributor.author | O'Donoghue, AnnMarie C. | |
dc.contributor.author | Smith, Andrew D. | |
dc.date.accessioned | 2013-05-03T12:31:01Z | |
dc.date.available | 2013-05-03T12:31:01Z | |
dc.date.issued | 2013 | |
dc.identifier | 51875986 | |
dc.identifier | 94a101d6-c446-4dc4-bfd9-6d1b6283f433 | |
dc.identifier | 000315597900015 | |
dc.identifier | 84874593137 | |
dc.identifier.citation | Collett , C J , Massey , R S , Maguire , O R , Batsanov , A S , O'Donoghue , A C & Smith , A D 2013 , ' Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions : role of the N-aryl substituent ' , Chemical Science , vol. 4 , no. 4 , pp. 1514-1522 . https://doi.org/10.1039/c2sc22137c | en |
dc.identifier.issn | 2041-6520 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/36567526 | |
dc.identifier.uri | https://hdl.handle.net/10023/3509 | |
dc.description.abstract | The in situ observation, isolation and reversible formation of intermediate 3-(hydroxybenzyl) azolium salts derived from NHC addition to a range of substituted benzaldehydes is probed. Equilibrium constants for the formation of these 3-(hydroxybenzyl) azolium salts, as well as rate constants of hydrogen-deuterium exchange (k(ex)) at C(alpha) of these intermediates for a range of N-aryl triazolinylidenes is reported. These combined studies give insight into the preference of N-pentafluorophenyl NHCs to participate in benzoin and Stetter reaction processes. | |
dc.format.extent | 9 | |
dc.format.extent | 452869 | |
dc.language.iso | eng | |
dc.relation.ispartof | Chemical Science | en |
dc.subject | Heterocyclic carbene | en |
dc.subject | Thiazolium salts | en |
dc.subject | Michael addition | en |
dc.subject | Triazolium salts | en |
dc.subject | Umpolung reaction | en |
dc.subject | Nucleophilic carbenes | en |
dc.subject | Breslow intermediate | en |
dc.subject | Alpha,beta-unsaturated aldehydes | en |
dc.subject | Thiamine action | en |
dc.subject | Homoenolate equivalents | en |
dc.subject | QD Chemistry | en |
dc.subject.lcc | QD | en |
dc.title | Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions : role of the N-aryl substituent | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 10.1039/c2sc22137c | |
dc.description.status | Peer reviewed | en |
This item appears in the following Collection(s)
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.