Journal of Organic Chemistry p. 3419 - 3422 (1995)
Update date:2022-08-10
Topics:
Petrov, Viacheslav A.
Davidson, Fred
Smart, Bruce E.
Polyfluorinated oxetanes are prepared in high yields by an electrophilic <2+2> cycloaddition reaction between hexafluoroacetone and fluorinated ethylenes that is catalyzed by an anhydrous aluminum chlorofluoride Lewis acid.The reaction is regiospecific with hydrofluoroethylenes CHX=CF2 (X = H, F, Cl, Br), whereas halotrifluoroethylenes CFX=CF2 (X = Cl, Br) give nearly equal amounts of the isomeric oxetanes.Hexafluoropropylene oxide, which rapidly rearranges under the reaction conditions, can be substituted for hexafluoroacetone in this new oxetane synthesis.
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