New Search

Export article
Open Access

Kinetic and Structure‐Activity Studies of the Triazolium Ion‐ Catalyzed Intramolecular Stetter Reaction

Christopher J. Collett, Claire. M. Young, Richard. S. Massey, Annmarie C. O'Donoghue,
Published: 7 May 2021
 by  Wiley
European Journal of Organic Chemistry ; doi:10.1002/ejoc.202100384

Abstract: Mechanistic studies of the triazolium ion‐catalyzed intramolecular Stetter reaction using initial rates analysis in NEt 3 /NEt 3 .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.
Keywords: NHC / Breslow intermediate / triazolium / Stetter reaction / initial rates analysis

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

Share this article

Click here to see the statistics on "European Journal of Organic Chemistry" .
References (33)
    Back to Top Top