Friedel-Crafts cyclization of 1,1-difluoroalk-1-enes:: Synthesis of benzene-fused cyclic ketones via α-fluorocarbocations

被引：38
|
作者：
Ichikawa, J [1 ]
Jyono, H
Kudo, T
Fujiwara, M
Yokota, M
机构：
[1] Univ Tokyo, Grad Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan
[2] Kyushu Inst Technol, Dept Appl Chem, Kitakyushu, Fukuoka 8048550, Japan
来源：
SYNTHESIS-STUTTGART | 2005年 / 01期
关键词：
Friedel-Crafts cyclization; difluoroalkene; bicyclic ketone; alpha-fluorocarbocation; fluoroalcohol solvent;
D O I：
10.1055/s-2004-834910
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,1-Difluoroalk-1-enes bearing a phenyl group at the C-3, -4, or -5 position, readily obtained from 2,2,2-trifluoroethyl p-toluenesulfonate, are treated with FSO3H.SbF5 to undergo Friedel-Crafts cyclization in (CF3)(2)CHOH. The cyclization takes place via alpha-fluorocarbocations. followed by spontaneous hydrolysis of the C-F bond to afford bicyclic ketones including a five, six, or seven-membered ring in good yield.
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页码：39 / 46
页数：8
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