Isolable Anionic, Neutral and Cationic Radicals from Reactions of N,N'-Dimesityldiamidocarbene and Lewis Acids

B(C₆ F₅ )₃ undergoes nucleophilic attack by N,N'-dimesityldiamidocarbene (DAC) with fluoride transfer to the boron center, resulting in a new zwitterion (1). This B-F fluoride can be replaced or abstracted to give the corresponding hydride (2) or triflate (3) derivatives or the corresponding cation (4). These species are reduced with KC₈ or Cp₂ Co to give isolable anionic and neutral radicals (5-8). Similarly, the [Ph₃ C] cation undergoes nucleophilic attack by DAC resulting in the spontaneous formation of the radical cation (9).