FORMATION AND ROLE OF CARBOCATIONS IN ELECTROLYTIC FLUORINATION USING HYDROGEN-FLUORIDE ELECTROLYTES IN A NAFION MEMBRANE-DIVIDED TEFLON CELL

A Nafion ® cation permselective membrane was used in anhydrous hydrogen fluorinde (AHF) in a series of electrofluorinations of organic compounds. The carbocations generated chemically and electrochemically in the anode compartment, crossed the membrane under the influence of electric field, and were quenched in the cathode compartment by suitable organic nucleophile. Products due to Friedel-Crafts type substitution, isomerization and polymerization were identified. An HF-pyridine (29%) complex was also examined as a possible electrolyte with platinum and carbon anodes. The extent of fluorination was small or none. Thus, neither a direct nor a ionic fluorination mechanism was operative in the process although the conditions appeared suitable for both. © 1979.