Bromination-mediated regioselective preparation of cyclopentadienyl-type [60]fullerene derivatives with alkoxy, peroxy, and bromo or hydro addends |
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| Authors: | Zhang Jianxin Xin Nana Gan Liangbing |
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| Institution: | Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China. |
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| Abstract: | Bromine reacts with the 1,2-bisadduct C(60)(OOtBu)(2) efficiently to form the cyclopentadienyl-type compound 4 (C(60)(OOtBu)(2)Br(4)). In the presence of AgClO(4), the four bromine atoms can be replaced regioselectively by methoxyl groups in a stepwise fashion to form C(60)(OOtBu)(2)Br(4-x)(OMe)(x). A second alcohol may be introduced by treating partially methoxylated compound 6 (C(60)(OOtBu)(2)Br(2)(OMe)(2)) with ROH/AgClO(4). Other related reactions have been investigated to explore the reactivity patterns. The structure of compound 6 was confirmed by single crystal X-ray analysis. |
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