AN UNUSUAL EXAMPLE OF STEREOELECTRONIC CONTROL IN THE RING-OPENING OF 3,3-DISUBSTITUTED 1,2-DICHLOROCYCLOPROPENES

被引：10

作者：

BAIRD, MS

ALDULAYYMI, JR

RZEPA, HS

THOSS, V

机构：

[1] UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND

[2] UNIV COLL N WALES,DEPT CHEM,BANGOR LL57 2UW,GWYNEDD,WALES

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1992年 / 18期

关键词：

D O I：

10.1039/c39920001323

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Quantitative SCF-MO calculations at the PM3 and ab initio level reveal that the origin of the stereoselective ring opening of 1,2-dichloro-3,3-disubstituted cyclopropenes (1, R2 = CH2Cl, CH2OMe or CH2Ph) to give vinylcarbenes 2 via transition state 5 arises from stereoelectronic control, in contrast to that of cyclopropenes having bulky non-polar substituents such as R2 = Pr(i) which favours a less hindered transition state 6.

引用

页码：1323 / 1325

页数：3

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