The Complete Mechanism of an Aldol Condensation

Although aldol condensation is one of the most important organic reactions, capable of forming new C–C bonds, its mechanism has never been fully established. We now conclude that the rate-limiting step in the base-catalyzed aldol condensation of benzaldehydes with acetophenones, to produce chalcones...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-07, Vol.81 (13), p.5631-5635
Main Authors: Perrin, Charles L, Chang, Kuei-Lin
Format: Article
Language:English
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Summary:Although aldol condensation is one of the most important organic reactions, capable of forming new C–C bonds, its mechanism has never been fully established. We now conclude that the rate-limiting step in the base-catalyzed aldol condensation of benzaldehydes with acetophenones, to produce chalcones, is the final loss of hydroxide and formation of the CC bond. This conclusion is based on a study of the partitioning ratios of the intermediate ketols and on the solvent kinetic isotope effects, whereby the condensations are faster in D2O than in H2O, regardless of substitution.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00959