845777-11-9Relevant articles and documents
Friedel-crafts cyclization of 1,1-difluoroalk-1-enes: Synthesis of benzene-fused cyclic ketones via α-fluorocarbocations
Ichikawa, Junji,Jyono, Hideharu,Kudo, Takao,Fujiwara, Masaki,Yokota, Misaki
, p. 39 - 46 (2007/10/03)
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)2CHOH. The cyclization takes place via α-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.