Unexpected reactions of [60]fullerene involving tertiary amines and insight into the reaction mechanisms |
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Authors: | Wang Guan-Wu Chen Xiao-Ping Cheng Xin |
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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, China. gwang@ustc.edu.cn |
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Abstract: | Thermal reactions of 60]fullerene with amino acid ester hydrochlorides and triethylamine in o-dichlorobenzene at reflux afforded pyrrolidinofullerene derivatives containing the CH(3)CH moiety and originating from triethylamine through an unusual C-N bond cleavage. Detailed investigation of these thermal reactions resulted in the discovery of unprecedented reactions between C(60) and tertiary amines and of reactions of C(60) with tertiary amines and aldehydes, giving cyclopentafullerene derivatives with high stereoselectivity. Plausible reaction mechanisms for the product formation involving the uncommon C-N bond cleavage of tertiary amines were proposed on the basis of extensive experimental results. |
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Keywords: | [60]fullerene amino acids cycloaddition reaction mechanisms tertiary amines |
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