ELECTRONIC EFFECTS IN PI-FACIALLY STEREOSELECTIVE EPOXIDATION OF PHENYLTRIFLUOROMETHYLPROPENOL

被引:10
作者
CASHER, O [1 ]
OHAGAN, D [1 ]
ROSENKRANZ, CA [1 ]
RZEPA, HS [1 ]
ZAIDI, NA [1 ]
机构
[1] UNIV DURHAM,DEPT CHEM,DURHAM DM1 3LE,ENGLAND
关键词
D O I
10.1039/c39930001337
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
AM1, PM3 and ab initio 6-31G* calculations indicate that stereoselective epoxidation of the alkene 3 arises from stereoelectronic control exerted via a CF3-C bond orientated anti to the alkene plane for steric reasons, in contrast to a previously proposed model for epoxidation of allylic fluorides in which the F-C and alkene bonds are oriented syn.
引用
收藏
页码:1337 / 1340
页数:4
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