Hydroxide-Initiated Conversion of Aromatic Nitriles to Imidazolines: Fullerenes vs TCNE

Transformation of aromatic nitriles to imidazolines has been achieved under basic conditions with the electron-deficient C-60 and C-70 fullerenes, but not with the electron-deficient olefin of tetracyanoethylene (TCNE). In situ UV-vis-NIR indicates that the ability of RC60- to undergo single-electron transfer (SET) to C-60 is crucial for the reaction.