Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 13, Pages 5631-5635Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00959
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Funding
- National Science Foundation [CHE11-48992]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1148992] Funding Source: National Science Foundation
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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.
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