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

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 01期

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

页码：147 / 150

页数：4

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