Nitrogen-containing compounds have been subjected to electrochemical oxidation with Et 3 N-3HF as an electrolyte. Caffeine afforded 8-fluorocaffeine as a sole product in 40.3% yield. Guanosine tetraacetate and uridine triacetate gave the fluorinated compounds in 17.5 and 4.6% yields, rspectively. Similar electrochemical oxidation of caffeine with methanol, KCl, or KCN afforded 8-methoxycaffeine, 8-chlorocaffeine, or 8-cyanocaffeine, respectively.
