Organic letters

Baylis-Hillman mechanism: a new interpretation in aprotic solvents

KE Price, SJ Broadwater, HM Jung, DT McQuade

文献索引：Price, Kristin E.; Broadwater, Steven J.; Jung, Hyun M.; McQuade, D. Tyler Organic Letters, 2005 , vol. 7, # 1 p. 147 - 150

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被引用次数: 199

摘要

Using reaction rate data collected in aprotic solvents, we have determined that the Baylis- Hillman rate-determining step is second order in aldehyde and first order in DABCO and acrylate. On the basis of these data, we have proposed a new mechanism involving a hemiacetal intermediate. The proposed mechanism was then supported using two different kinetic isotope experiments.