Synthesis of C60-fused tetrahydrothiophene derivatives via nucleophilic cycloaddition of thiocyanates |
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Authors: | Wang Guan-Wu Li Jia-Xing 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: | Nucleophilic cycloaddition of thiocyanates 1a-e with C60 in the presence of 1,8-diazabicyclo5.4.0]undec-7-ene afforded C60-fused 2-iminotetrahydrothiophene derivatives 2a-e and methanofullerenes 3a-d. The product distributions were highly sensitive to the substrates employed. The 2-iminotetrahydrothiophene derivatives 2a-e could be further manipulated by hydrolysis and acetylation to give 2-oxotetrahydrothiophene derivatives 4a-e and 2-acetamidotetrahydrothiophene derivatives 5a-e. A possible reaction mechanism for the formation of products 2a-e and 3a-d was proposed. |
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