Reduction potential as a measure of activity of the N-F fluorinating agents

The possibility of evaluating activity of fluorinating agents by their electrochemical characteristics is confirmed by the example of N-fluorobenzenesulfoneimide (1), as well as 1-chlormethyl-4-fluoro-1,4-diazoniumbicyclo[2.2.2]octane (II) and 1-hydroxy-4-fluoro-1,4-diazoniumbicyclo[2.2.2]octane (III) ditetrafluoroborates. The half-wave potential E-1/2 of reduction on a rotating platinum electrode is the best activity measure. Compounds II and III, being very reactive fluorinating agents, are characterized by positive E-1/2. Compound I, which has moderate reactivity, reduces at much more negative potentials.