Journal of Organic Chemistry p. 1394 - 1399 (1985)
Update date:2022-08-11
Topics:
Kariv-Miller, Essie
Vajtner, Zlatko
The electroreduction of 1,3-difluorobenzene and fluorobenzene on mercury cathodes in diglyme was investigated.In preparative experiments using tetrabutylammonium tetrafluoroborate as the electrolyte, fluorobenzene formed benzene and 1,3-difluorobenzene formed a mixture of fluorobenzene and benzene.When dimethylpyrrolidinium (DMP+) tetrafluoroborate was used, benzene was obtained from fluorobenzene but the electrode potential was less negative.In the reduction of 1,3-difluorobenzene, a similar effect of DMP+ on the potential was observed.In addition, conditions were found for selective defluorination to fluorobenzene.Results from preparative experiments-products and reaction potentials-and cyclic voltammetry indicate that reductive defluorination in the presence of DMP+ is catalytic and mercury from the electrode seems to be involved.A possible mechanism is discussed.
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