J. Org. Chem. 2005, 70, 3980-3987

A new interpretation of the Baylis-Hillman mechanism

J. Org. Chem. 2005, 70, 3980-3987

Price KE, Broadwater SJ, Walker BJ, McQuade DT


On the bass 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.