Theoretical studies on cycloaddition reactions between keteniminium cations and olefins

被引：34

作者：

Ding, WJ ^{[1
]}

Fang, DC ^{[1
]}

机构：

[1] Beijing Normal Univ, Dept Chem, Beijing 100875, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 20期

关键词：

D O I：

10.1021/jo010461i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanisms of seven reactions between keteniminium cations and olefins have been theoretically explored at BHandHLYP/6-31G* level. It is found that these seven reactions always form a relatively stable hydrogen-bonded type of ion-molecule complex first except for reactions 1d+2a and 1e+2a, which have no hydrogen atom attached to nitrogen atom in keteniminium. cations. Some reactions take place via a concerted but unsynchronous mechanism, and the others are stepwise processes. The substituent effects are also studied. The data reveal that the electron-pushing substituents on keteniminium. cations disfavor the reaction, and the electron-attracting substituents on keteniminium cations favor the reactions. The substituent effects on ethene are contrary to the former case.

引用

页码：6673 / 6678

页数：6

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