Novel cycloaddition reaction of [60]fullerene with carbonyl ylides generated from epoxides |
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| Authors: | Wang Guan-Wu Yang Hai-Tao Wu Ping Miao Chun-Bao Xu Yu |
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| Institution: | 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 |
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| 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. |
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