Novel Cycloaddition Reaction of Fullerene with Carbonyl Ylides Generated from Epoxides
journal contributionposted on 26.05.2006, 00:00 authored by Guan-Wu Wang, Hai-Tao Yang, Ping Wu, Chun-Bao Miao, Yu Xu
The thermal reaction of 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.