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
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
收藏
页码:3980 / 3987
页数:8
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