Reactions of diethylcarbamoyl-lithium and bis(diethylcarbamoyl)mercury with highly fluorinated substrates

Nucleophilic acylations have been carried out using a species reacting as diethylcarbamoyl-lithium. With pentafluorobenzaldehyde it gave the addition product, N,N-diethylpentafluoromandelamide, and with hexafluorobenzene, octafluorotoluene, decafluorocyclohexene and pentadecafluoro-octanoyl chloride it gave products which are formed by the nucleophilic replacement of fluorine or chlorine by the -CONEt₂ group, though in poor yield. Reaction of bis(diethylcarbamoyl)mercury with decafluorocyclohexene, pentafluorobenzyl chloride and pentadecafluoro-octanoyl chloride afforded aminated products in low yields.