Massey, Richard S.; Murray, Jacob; Collett, Christopher J.; Zhu, Jiayun; Smith, Andrew D.; O’Donoghue, AnnMarie C. published the artcile< Kinetic and structure-activity studies of the triazolium ion-catalysed benzoin condensation>, Category: esters-buliding-blocks, the main research area is benzaldehyde triazolium catalyst preparation benzoin condensation reaction kinetics.
Steady-state kinetic and structure-activity studies of a series of six triazolium-ion pre-catalysts 2a-2f were investigated for the benzoin condensation. These data provide quant. insight into the role of triazolium N-aryl substitution under synthetically relevant catalytic conditions in a polar solvent environment. Kinetic behavior was significantly different to that previously reported for a related thiazolium-ion pre-catalyst 1, with the observed leveling of initial rate constants to νmax at high aldehyde concentrations for all triazolium catalysts. Values for νmax for 2a-2f increase with electron withdrawing N-aryl substituents, in agreement with reported optimal synthetic outcomes under catalytic conditions, and vary by 75-fold across the series. The leveling of rate constants supports a change in rate-limiting step and evidence supports the assignment of the Breslow-intermediate forming step to the plateau region. Correlation of νmax reaction data yielded a pos. Hammett ρ-value (ρ = +1.66) supporting the build up of electron d. adjacent to the triazolium N-Ar in the rate-limiting step favored by electron withdrawing N-aryl substituents. At lower concentrations of aldehyde, both Breslow-intermediate and benzoin formation are partially rate-limiting.
Organic & Biomolecular Chemistry published new progress about Benzoin condensation reaction. 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Category: esters-buliding-blocks.
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