Novel Cycloaddition Reaction of [60]Fullerene with Carbonyl Ylides Generated from Epoxides

The thermal reaction of [60]fullerene (C₆₀) with the carbonyl ylides generated in situ from trans-epoxides to give C₆₀-fused tetrahydrofuran derivatives has been investigated. The reaction of C₆₀ with trans-2-benzoyl-3-aryloxiranes afforded only cis-products, while the reaction of C₆₀ with 2-cyano-2-ethoxycarbonyl-3-aryloxiranes gave exclusively or predominantly cis isomers. The isomeric distributions of the latter reactions were drastically affected by the substituent on the phenyl ring.