Synthesis of Open-Cage [60]Fullerenes with Five Carbonyl Groups on the Rim of the 15-Membered Orifice

A new type of open-cage [60]fullerene was prepared starting from our previously reported open-cage [60]fullerenes containing hydroxy and tert-butylperoxo groups, and an iminofuranone moiety on the rim of the orifice. The key reactions are alcoholysis with MeOH/PCl5 and reductive aromatization with SnCl2 or HI (aq). The resulting open-cage compound contains two ketone carbonyls, two amide carbonyls, and one ester carbonyl group. The X-ray crystal structure of the precursor compound shows that the 18-membered orifice is almost completely blocked because of the presence of the amide group directly above the orifice.