Alternative Access to Cyclopentafullerenes through the Reaction of [60]Fullerene with Aldehydes and Secondary Amines.

A series of cyclopentafullerenes have been synthesized in high stereoselectivity by the thermal reaction of [60]fullerene with aldehydes and secondary amines. Both α,β-unsaturated aldehydes and saturated aldehydes can be utilized to synthesize cyclopentafullerenes as the cis isomers. The possible reaction mechanisms for the formation of cyclopentafullerenes are proposed on the basis of the experimental results.