A new interpretation of the Baylis-Hillman mechanism

被引：212

作者：

Price, KE ^{[1
]}

Broadwater, SJ ^{[1
]}

Walker, BJ ^{[1
]}

McQuade, DT ^{[1
]}

机构：

[1] Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 10期

关键词：

D O I：

10.1021/jo050202j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3980 / 3987

页数：8

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