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 ofN-fluorobenzenesulfoneimide (I), as well as l-chlormethyl-4-fluoro-l,4-diazoniumbicyclo [2.2.2]octane (II) and l-hydroxy-4-fluoro-l,4-diazoniumbicyclo[2.2.2]octane (III) ditetrafluoroborates. The half-wave potentialE _1/2 of reduction on a rotating platinum electrode is the best activity measure. CompoundsII andIII, being very reactive fluorinating agents, are characterized by positiveE _1/2. Compound I, which has moderate reactivity, reduces at much more negative potentials.