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Anodic fluorination of N-(diphenylmethyleneamino)-2,2,2-trifluoroethane and N-[bis(methylthio)methyleneamino]-2,2,2-triphenylethane in acetonitrile containing poly(HF) salt ionic liquids afforded monofluorinated products in moderate to good yields. On the other hand, anodic fluorination of N-[bis(methylthio)methylene]glycine methyl ester provided mono- and difluoroproducts depending on the amount of electricity passed. This is the first successful electrochemical fluorination of open-chain α-amino acid derivatives. Cathodic Michael addition of N-(diphenylmethyleneamino)-2,2,2-trifluoroethane to activated olefins such as acrylate and acrylonitrile was also successfully carried out using a titanium cathode.