Selective anodic fluorination of electrophilic alkenes

Anodic fluorination of some electrophilic alkenes (conjugated with electron-withdrawn groups), ethyl cinnamates, RC6H4CHCHCO2Et (R = H, CH3, CH3O, F and CF3), cinnamonitrile, C6H4CHCHCN, phenyl stryryl ketone, and t-butyl styryl ketone using ammonium fluorides as the fluorine source and supporting electrolyte, in CH2Cl2 as electrolytic solvent yields the expected vicinal difluoro compounds, as mixture of erythro and threo isomers. The anodic fluorination of phenyl 3,5-di-t-butyl-4-hydroxystyryl ketone yields two monofluoro compounds. A possible reaction mechanism is discussed.