Sequential photo-addition of glycine methyl-ester to [60]fullerene

While direct photo-addition of glycine-methyl-esters (GME) to [60]fullerene (C60) can yield a complex product mixture, only a fulleropyrrolidine (FP) mono-adduct has been characterized and the mechanism remains to be ascertained. We show here that visible light irradiation of a mixture of C60 and GME in the presence of oxygen is a direct route to synthesize sequentially higher FP poly-adducts through an unprecedented cyclization–deamination mechanism. Each step of this mechanism leads to a FP adduct involving the correlated addition of two GME radicals and the departure of an ammonia molecule.