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

B(C6F5)(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 Cp2Co to give isolable anionic and neutral radicals (5-8). Similarly, the [Ph3C] cation undergoes nucleophilic attack by DAC resulting in the spontaneous formation of the radical cation (9).