Synthesis of Arylvinyl-Substituted Fulleropyrrolidines: Novel Reaction of [60]Fullerene with Cinnamaldehydes and Amines

Abstract

A simple one-step reaction of [60]fullerene with cinnamaldehydes and primary/secondary amines without the addition of any inorganic salts afforded rare arylvinyl-substituted fulleropyrrolidines in moderate to good yields with high stereoselectivity. Secondary amines produced N-alkyl-2/5-arylvinyl fulleropyrrolidines with a preference of trans isomers as major products, while primary amines exclusively gave 2-aryl-5-arylvinyl fulleropyrrolidines as cis isomers. A plausible formation mechanism for fulleropyrrolidines was proposed to elucidate the above reaction process.