Journal of Organic Chemistry p. 2873 - 2877 (1989)
Update date:2022-08-04
Topics:
Stahly, G. Patrick
Bell, Donald R.
Triethyl(trifluoromethyl)silane and tri-n-butyl(trifluoromethyl)silane were found to react with quinones by addition to one of the carbonyl carbon atoms, giving dienones containing geminal trifluoromethyl and trialkylsiloxy substituents.These reactions were catalyzed by a variety of basic compounds.Quinones found to undergo this process include 1,2- and 1,4-benzoquinones (some bearing alkyl substituents), naphthoquinone, anthraquinone, and phenanthrenequinone.Most of the resulting dienones gave (trifluoromethyl)phenols on dissolving matal reduction, and one was subjected to reductive amination to give (trifluoromethyl)aniline.
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