Electrochemical fluorination of N-chloroalkyl-substituted cyclic amines

Add time:07/21/2019    Source:sciencedirect.com

The electrochemical fluorination of such N-chloroalkyl substituted cyclic amines as N-chloromethylpyrrolidine (1), N-(3-chloropropyl)pyrrolidine (2), N-chloromethylpiperidine (3), N-(2-chloroethyl)piperidine (4), N-(3-chloropropyl)piperidine (5), N-chloromethylmorpholine (6), N-(3-chloropropyl)morpholine (7), N-(2-chloroallyl)morpholine (8) has been conducted. Except in the cases of the N-chloromethyl-substituted ones (1,3 and 6), the corresponding chlorine-retaining-perfluoroamines were obtained in a yield of 5 ∼ 20% together with perfluorinated ones (Yield = 20 ∼ 60%). Neither chlorine-retaining amines nor perfluorinated amines, both of which having the original skeleton, was produced from fluorinations of 1,3 and 6 in an appreciable yield. The spectroscopic data and physical properties of newly synthesized perfluoro-N-chloroalkyl-substituted cyclic amines are presented.

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