Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 10, Pages 3980-3987Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo050202j
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On the basis of reaction rate data, we have proposed a new mechanism for the Baylis-Hillman reaction involving the formation of a hemiacetal intermediate. We have determined that the rate-determining step is second order in aldehyde and first order in DABCO and acrylate. We have shown that this mechanism is general to aryl aldehydes under polar, nonpolar, and protic conditions using both rate data and two isotope effect experiments.
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