Hydroxide-initiated conversion of aromatic nitriles to imidazolines: fullerenes vs TCNE.

ABSTRACT

Transformation of aromatic nitriles to imidazolines has been achieved under basic conditions with the electron-deficient C60 and C70 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 C60 is crucial for the reaction.