Addition of Electron-Rich Aromatics to Azafullerenium Carbocation. A Stepwise Electrophilic Substitution Mechanism
Date
2003ISSN
1523-7060Source
Organic lettersVolume
5Issue
24Pages
4603-4606Google Scholar check
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(Matrix presented) 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 C 59N+ on the aromatic ring in the first step of the reaction, followed by hydrogen abstraction in a rate-determining second step.