Journal of Fluorine Chemistry p. 187 - 190 (1997)
Update date:2022-08-03
Topics:
Dmowski, Wojciech
Kozlowski, Tomasz
Treatment of (1R,3S)-(+)-camphoric acid (1) with sulphur tetrafluoride at ambient temperature gives, in general, three products: 1,2,2-trimethyl-3-trifluoromethyl-1-cyclopentanoyl fluoride (2), 2,2,4,4-tetrafluoro-1,8,8-trimethyl-3-oxa-bicyclo[3.2.1]octane (3) and camphoroyl difluoride (4). The ratio of products strongly depends on the reaction time. Alkaline hydrolysis of (2) gives 1,2,2-trimethyl-3-trifluoromethyl-1-cyclopentanecarboxylic acid (5), quantitatively. All products exhibit optical activity.
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Doi:10.1039/jr9550000405
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