Synthesis of 2-AryI-5-alkyl-fulleropyrrolidines: Metal-Free-Mediated Reaction of [60]Fullerene with Aromatic Aldehydes and Inactive Primary Amines

The metal-free-mediated thermal reaction of [60]fullerene with aromatic aldehydes and inactive primary amines bearing electron-donating groups at the alpha-position afforded a series of 2-aryl-5-alkyl-fulleropyrtolidines, including the scarce 27 aryl-5-benzyl-fulleropyrrolidines as a mixture of cis and trans isomers. With rare exceptions, the mixture of, cis, and trans isomers could be easily isolated by column chromatography, with a preference of cis isomers as Major products. A plausible mechanism for the formation of fulleropyrrolidines is also proposed.