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.
Wang
Guan-Wu
GW
Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China. gwang@ustc.edu.cn
Wu
Ping
P
Yang
Hai-Tao
HT