Unexpected fullerene dimerization via [5,6]-bond upon functionalization of C(s)-C70(CF3)8 by the Bingel reaction |
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Authors: | Ovchinnikova Natalia S Goryunkov Alexey A Khavrel Pavel A Belov Nikita M Apenova Marina G Ioffe Ilya N Yurovskaya Marina A Troyanov Sergey I Sidorov Lev N Kemnitz Erhard |
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Institution: | Chemistry Department, Moscow State University, Leninskie Gory, 119991, Moscow, Russia. nso@thermo.chem.msu.ru |
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Abstract: | The Bingel reaction of the C(s) isomer of C(70)(CF(3))(8) has been found to yield two C(70)(CF(3))(8)C(CO(2)Et)(2)] monoadducts and one C(70)(CF(3))(8)C(CO(2)Et)(2)](2) bisadduct as its major products. Malonate addition occurs at those 6,6]-bonds that radiate from the polar pentagons of the C(70)(CF(3))(8) cage. Unexpectedly, X-ray single crystal analysis reveals dimerization of the above substances during crystallization, providing two isomers of {C(70)(CF(3))(8)C(CO(2)Et)(2)]}(2), one isomer of {C(70)(CF(3))(8)C(CO(2)Et)(2)](2)}(2) and {C(70)(CF(3))(8)}(2). This dimerization represents 2+2]-cycloaddition via 5,6]-bonds and results in functionalization patterns resembling several known C(70)X(10) derivatives. |
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