Geminal bond participation in the electrocyclic reactions: Torquoselectivities of silyl and trimethylsilyl derivatives of cyclobutene, iminocyclobutene, and cyclobutenone

被引：44

作者：

Ikeda, H ^{[1
]}

Kato, T ^{[1
]}

Inagaki, S ^{[1
]}

机构：

[1] Gifu Univ, Fac Engn, Dept Chem, Gifu 5011193, Japan

来源：

CHEMISTRY LETTERS | 2001年 / 03期

关键词：

D O I：

10.1246/cl.2001.270

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Analysis of the bond interactions at the transition state of the electrocyclic reaction of cyclobutene shows significant participation of the inward- and outward-rotating a bonds geminal to the reacting centers. Electron-donating capabilities of the inward-rotating a bonds are predicted to accelerate the reactions. The prediction of the torquoselectivities is confirmed by calculated preference of the inward rotations of the silyl and trimethylsilyl groups in cyclobutene, iminocyclobutene, and cyclobutenone.

引用

页码：270 / 271

页数：2

共 12 条

[1]

Brownlee R. T. C., 1973, PROGR PHYS ORG CHEM, V10, P1, DOI DOI 10.1002/9780470171899.CH1

[2] Electronic control of stereoselectivities of electrocyclic reactions of cyclobutenes: A triumph of theory in the prediction of organic reactions [J].