Electrophilicities of Bissulfonyl Ethylenes

被引：25

作者：

Asahara, Haruyasu ^{[1
]}

Mayr, Herbert ^{[1
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2012年 / 7卷 / 06期

关键词：

electrophilicity; kinetics; linear free-energy relationship; Michael additions; sulfones; ALPHA; BETA-UNSATURATED IMINIUM IONS; ORGANOCATALYTIC CONJUGATE ADDITION; ASYMMETRIC MICHAEL ADDITION; POLAR ORGANIC-REACTIVITY; VINYL SULFONES; ALDEHYDES; PARAMETERS; NUCLEOPHILICITY; SCALES; COMBINATIONS;

D O I：

10.1002/asia.201101046

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Kinetics of the reactions of bissulfonyl ethylenes with various carbanions, a sulfur ylide, and siloxyalkenes have been investigated photometrically at 20 degrees C. The second-order rate constants have been combined with the known nucleophile- specific parameters N and sN for the nucleophiles to calculate the empirical electrophilicity parameters E of bissulfonyl ethylenes according to the linear free energy relationship log k(20 degrees C)=sN(N+E). Structure-reactivity relationships are discussed, and it is shown that the electrophilicity parameters E derived in this work can be employed to define the synthetic potential of bissulfonyl ethylenes as Michael acceptors.

引用

页码：1401 / 1407

页数：7

共 69 条

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