Unexpected fullerene dimerization via [5,6]-bond upon functionalization of C(s)-C70(CF3)8 by the Bingel reaction

Autor: Lev N. Sidorov, Sergey I. Troyanov, Ilya N. Ioffe, Erhard Kemnitz, Alexey A. Goryunkov, Marina G. Apenova, Pavel A. Khavrel, N. S. Ovchinnikova, Marina A. Yurovskaya, Nikita M. Belov
Rok vydání: 2010
Předmět:
Zdroj: Dalton transactions (Cambridge, England : 2003). 40(4)
ISSN: 1477-9234
Popis: 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.
Databáze: OpenAIRE