Reaction of nitroalkanes with polyfluoroaromatic compounds

Nitromethane and nitroethane in the presence of DBU attack preferentially the para position of pentafluorobenzonitrile and methyl pentafluorobenzoate to give the addition products in good yield. The resulting nitro compounds can be converted to tetrafluorotoluene or ethyl benzene derivatives by tri-n-butyltin hydride. TiCl3 solution neatly transforms the nitroethyl compounds into corresponding ketones. With a base, the nitro compounds can be used to extend chain length using Michael acceptors like ethyl acrylate and acrylonitrile.