Issue 4, 2011
From the journal:

Dalton Transactions

Unexpected fullerene dimerizationvia [5,6]-bond upon functionalization of Cs-C70(CF3)8 by the Bingel reaction†

Natalia S. Ovchinnikova,*a   Alexey A. Goryunkov,a   Pavel A. Khavrel,a   Nikita M. Belov,a   Marina G. Apenova,a   Ilya N. Ioffe,a   Marina A. Yurovskaya,a   Sergey I. Troyanov,a   Lev N. Sidorova  and  Erhard Kemnitzb  

* Corresponding authors

a Chemistry Department, Moscow State University, Leninskie Gory, Moscow, Russia
E-mail: nso@thermo.chem.msu.ru
Fax: +7 (495) 939-12-40
Tel: +7 (495) 939-53-73

b Institute of Chemistry, Humboldt University Berlin, Brook-Taylor-Str-2, 12489 Berlin, Germany

Abstract

The Bingel reaction of the Cs isomer of C70(CF3)8 has been found to yield two C70(CF3)8[C(CO2Et)2] monoadducts and one C70(CF3)8[C(CO2Et)2]2 bisadduct as its major products. Malonate addition occurs at those [6,6]-bonds that radiate from the polar pentagons of the C70(CF3)8 cage. Unexpectedly, X-ray single crystal analysis reveals dimerization of the above substances during crystallization, providing two isomers of {C70(CF3)8[C(CO2Et)2]}2, one isomer of {C70(CF3)8[C(CO2Et)2]2}2 and {C70(CF3)8}2. This dimerization represents [2+2]-cycloaddition via [5,6]-bonds and results in functionalization patterns resembling several known C70X10 derivatives.

Graphical abstract: Unexpected fullerene dimerizationvia [5,6]-bond upon functionalization of Cs-C70(CF3)8 by the Bingel reaction

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Article information

DOI
https://doi.org/10.1039/C0DT00777C
Article type
Paper
Submitted
02 Jul 2010
Accepted
29 Oct 2010
First published
09 Dec 2010

Dalton Trans., 2011,40, 959-965

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Unexpected fullerene dimerizationvia [5,6]-bond upon functionalization of Cs-C70(CF3)8 by the Bingel reaction

N. S. Ovchinnikova, A. A. Goryunkov, P. A. Khavrel, N. M. Belov, M. G. Apenova, I. N. Ioffe, M. A. Yurovskaya, S. I. Troyanov, L. N. Sidorov and E. Kemnitz, Dalton Trans., 2011, 40, 959 DOI: 10.1039/C0DT00777C

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