title: Novel cycloaddition reaction of [60]fullerene with carbonyl ylides generated from epoxides.
abstract: 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.
authors.affiliation: 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
authors.forename: Guan-Wu
authors.initials: GW
authors.lastname: Wang
authors.forename: Hai-Tao
authors.initials: HT
authors.lastname: Yang
authors.forename: Ping
authors.initials: P
authors.lastname: Wu
authors.forename: Chun-Bao
authors.initials: CB
authors.lastname: Miao
authors.forename: Yu
authors.initials: Y
authors.lastname: Xu
mesh_terms: D004852:Epoxy Compounds / Q000737:chemistry*; D037741:Fullerenes / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D004852:Epoxy Compounds; D037741:Fullerenes; D005663:Furans; C069837:fullerene C60