THE ELECTROCHEMICAL FLUORINATION OF NITROGEN-CONTAINING CARBOXYLIC-ACIDS - FLUORINATION OF DIMETHYLAMINO-SUBSTITUTED OR DIETHYLAMINO-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES

The electrochemical fluorination of six derivatives of dimethylamino- or diethylamino-substituted carboxylic acids has been conducted. As the main fluorination products, cyclized and cleaved products as well as the desired N-containing perfluoroacid fluorides were formed, and their ratios depended on the chain length and the structure of the starting carboxylic acids, and the nature of the dialkylamino group. Through this work, perfluoro(dimethylamino-acetyl fluoride), perfluoro(diethylamino- acetyl fluoride), perfluoro(2-dimethylamino-propionyl fluoride), perfluoro(2-dimethylamino-butyryl fluoride) and perfluoro(3-dimethylamino-propionyl fluoride) were prepared. Except for perfluoro(dimethylamino-acetyl fluoride), these acid fluorides were new compounds. The physical properties of new compounds obtained including these acid fluorides are reported together with their spectral (19F nmr, Mass and IR) data. © 1990.