TEMPERATURE EFFECTS ON THE STEREOCHEMISTRY OF THE SOLVOLYSIS OF TRANS-2,3-DIPHENYLOXIRANE

被引：7

作者：

INOUE, M ^{[1
]}

TAGUCHI, Y ^{[1
]}

SUGITA, T ^{[1
]}

ICHIKAWA, K ^{[1
]}

机构：

[1] KYOTO UNIV, FAC ENGN, DEPT HYDROCARBON CHEM, KYOTO 606, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1979年 / 52卷 / 06期

关键词：

D O I：

10.1246/bcsj.52.1743

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The temperature effects on the stereochemistry of the acid-catalyzed ethanolysis of irawj-2, 3-diphenyloxirane were examined. The stereochemistry of the reaction became more retentive as the reaction temperature was raised. The reaction mechanisms are discussed, and it is concluded that concurrent reactions take place in the ethanolysis, one of them giving an inverted product, and the other, a retained one, and that the former reaction is caused by a nucleophilic attack of ethanol on the carbon of the conjugate acid of the epoxide, while the latter proceeds via an intermediate which has a carbonium-ion character.

引用

页码：1743 / 1747

页数：5

共 23 条

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