Addition of electron-rich aromatics to azafullerenium carbocation. A stepwise electrophilic substitution mechanism

The reaction between the C59N+ carbocation and the electron-rich aromatic compounds toluene and anisole has been mechanistically studied. The measured intermolecular kinetic isotope effects are consistent with an electrophilic aromatic substitution mechanism in which the arenium cation is formed by electrophilic attack of C59N+ on the aromatic ring in the first step of the reaction, followed by hydrogen abstraction in a rate-determining second step.