Electrochemical fluorination of the N-methylmorpholine

The results of some researches as regards the possibility to carry out selective electrochemical fluorinations of organic compounds by use of organic solvents are reported. Various organic solvents (acetonitrile, 1,4-dioxane, N,N-dimethylformamide) have been employed in the electrochemical fluorination of the N-methylmorpholine (NMM), but the results have not been those expected. Because of strong interactions taken place within certain ratios solvent/HF, many difficulties have been got into as regards the conductivity. Better results were obtained working without the solvent and with a great concentration (40 %) of the NMM in hydrogen fluoride. In the experiments carried out, the electrochemical fluorination of the NMM appeared highly selective: at first it took place on the positions beside the oxygen atom, then on those beside the nitrogen atom and at last on the methylic group. A mechanism of the reaction is proposed