MARKED LEAVING GROUP STRAIN IN (Z)-2-ETHYLIDENEBICYCLO[2.2.2]OCT-1-YL TRIFLATE AND ITS SIGNIFICANT RELIEF IN (Z)-2-ETHYLIDENEBICYCLO[3.2.2]NON-1-YL MESYLATE

被引：11

作者：

TAKEUCHI, K

OHGA, Y

KITAGAWA, T

机构：

[1] Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University, Sakyo-ku

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 17期

关键词：

D O I：

10.1021/jo00017a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rate of ethanolysis at 25-degrees-C of (Z)-2-ethylidenebicyclo[2.2.2]oct-1-yl triflate [(Z)-3] is 217 times faster than that of its E isomer, whereas more flexible (Z)-2-ethylidenebicyclo[3.2.2]non-1-yl mesylate solvolyzes 3.4 times slower than its E isomer, indicating marked leaving-group strain in the ground state of (Z)-3, which is supported by MM2 calculations.

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页码：5007 / 5008

页数：2

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