Revisiting the Perfluorinated Trityl Cation

Abstract

Although ultimately not isolable for X-ray structural characterization, the free perfluorinated trityl cation was shown to be observable in neat triflic acid, which represents milder conditions than previous reports of this cation in "magic acid" or oleum. A triflate-bound species could be generated in organic solvents using stoichiometric amounts of triflic acid and was shown to be synthetically viable for hydride abstraction from Et₃ SiH. It was demonstrated that the para-position on the -C₆ F₅ rings is the primary point of attack for decomposition of the cation.