Novel cycloaddition reaction of [60] fullerene with carbonyl ylides generated from epoxides

The thermal reaction of [60] fullerene (C-60) with the carbonyl ylides generated in situ from trans-epoxides to give C-60-fused tetrahydrofuran derivatives has been investigated. The reaction of C-60 with trans-2-benzoyl-3-aryloxiranes afforded only cis-products, while the reaction of C-60 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.