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.

引用

页码：39 / 46

页数：8

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