Journal
CHEMICAL SCIENCE
Volume 4, Issue 4, Pages 1514-1522Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2sc22137c
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Funding
- Royal Society
- EPSRC
- Engineering and Physical Sciences Research Council [EP/G013268/1] Funding Source: researchfish
- EPSRC [EP/G013268/1] Funding Source: UKRI
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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.
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