IN THE BLIND SPOT OF DIFFUSION CONTROL - 2-FLUOROALLYL CATIONS AND THEIR VARIOUS POSSIBILITIES FOR STABILIZATION

被引:5
作者
BESSIERE, Y
BESSARD, Y
KOTANI, T
SCHLOSSER, M
机构
[1] Institut de Chimie organique de l'Université, CH-1005 Lausanne
关键词
D O I
10.1016/S0040-4020(01)87104-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three new model substrates of the chlorofluorocyclopropane type (6, 11 and 14) were submitted to silver ion-assisted ring opening. No rearrangement, but only fragmentation or direct solvolysis was found to take place. In the latter case, primary rather than tertiary 2-fluoroallyl alcohols are formed almost exclusively. Nucleophilic attack at the unsubstituted terminus of the 2-fluoroallyl cation is apparently favored for steric reasons.
引用
收藏
页码:4355 / 4360
页数:6
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