Journal of Organic Chemistry p. 3909 - 3912 (1990)
Update date:2022-09-26
Topics:
Uneyama, Kenji
Watanabe, Shunsuke
Electrooxidation of trifluoroacetic acid in the presence of fumaronitrile (1) in an MeCN-H2O-(Pt) system provides 2-(trifluoromethyl)succinonitrile (2) in a 65percent yield.The electrochemical reaction is remarkably affected by the reaction temperature.That is, at the ice-cooling temperature, a simple hydrogenation of 1 predominates, while at 50-55 deg C, the desired hydrotrifluoromethylation proceeds exclusively.The anodically generated trifluoromethyl radicals recombine with the succinonitrile radicals produced at the cathode, leading to the formation of 2.
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