Baylis-Hillman mechanism: A new interpretation in aprotic solvents

被引:195
|
作者
Price, KE [1 ]
Broadwater, SJ [1 ]
Jung, HM [1 ]
McQuade, DT [1 ]
机构
[1] Cornell Univ, Dept Chem & Biol Chem, Ithaca, NY 14853 USA
关键词
D O I
10.1021/ol047739o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
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.
引用
收藏
页码:147 / 150
页数:4
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