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.
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, PR China. gwang@ustc.edu.cn
Yang
Hai-Tao
HT
Wu
Ping
P
Miao
Chun-Bao
CB
Xu
Yu
Y
D004852:Epoxy Compounds / Q000737:chemistry*; D037741:Fullerenes / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D015394:Molecular Structure
D004852:Epoxy Compounds; D037741:Fullerenes; D005663:Furans; C069837:fullerene C60