Reaction of [60]fullerene with trans-epoxides: a theoretical study.

The experimental results of the reaction of C60 with carbonyl ylides generated from trans-epoxides, which afforded cis-products exclusively or predominantly, can be explained well by computational investigation of the proposed reaction mechanism. Our theoretical calculations demonstrate that only cis-carbonyl ylides can be formed directly from trans-epoxides, in compliance with the Woodward-Hoffmann rule. Importantly, the ring opening of trans-epoxides, which is the rate-determining step, should be included in the whole reaction profiles to explain all experimental phenomena.