ELECTRONIC CONTROL OF THE STEREOCHEMISTRY OF ELECTROPHILIC AND NUCLEOPHILIC-ATTACK ON DOUBLE-BONDS IN 6-MEMBERED RINGS

被引：38

作者：

EISENSTEIN, O ^{[1
]}

KLEIN, J ^{[1
]}

LEFOUR, JM ^{[1
]}

机构：

[1] LAB CHIM THEOR, ORSAY, FRANCE

来源：

TETRAHEDRON | 1979年 / 35卷 / 02期

关键词：

D O I：

10.1016/S0040-4020(01)99485-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

CNDO and ab initio MO calculations reveal a deformation of the π* and π orbitals of cyclohexene in the axial directions, thus providing a reasonable explanation for the axial attack on cyclohexene either by electrophiles or by nucleophiles. It is shown in the case of 1-butene by an ab initio calculation that this orbital deformation is a result of the mixing of the π and σ orbitals of the double bond under the influence of the allylic C-C bond. © 1979.

引用

页码：225 / 228

页数：4

共 37 条

[1] STEREOCHEMISTRY OF NUCLEOPHILIC ADDITION-REACTIONS - ADDITION OF THIOPHENOL AND OF HYDROGEN-CHLORIDE TO 4-TERT-BUTYL-1-CYANOCYCLOHEXENE [J].