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.
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页码：1323 / 1325
页数：3
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