Issue 1, 2008
From the journal:

New Journal of Chemistry

Regioselective synthesis and crystal structure of C70(CF3)10[C(CO2Et)2]†

Nataliya S. Ovchinnikova,a   Daria V. Ignat’eva,a   Nadezhda B. Tamm,a   Stanislav M. Avdoshenko,a   Alexey A. Goryunkov,*a   Ilya N. Ioffe,a   Vitaliy Yu. Markov,a   Sergey I. Troyanov,a   Lev N. Sidorov,a   Marina A. Yurovskayaa  and  Erhard Kemnitzb  

* Corresponding authors

a Chemistry Department, Moscow State University, Leninskie Gory, Russia
E-mail: aag@thermo.chem.msu.ru
Fax: +7 495-939-1240
Tel: +7 495-939-5373

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

Abstract

The Bingel reaction of poly(trifluoromethyl)fullerene p7mp-C70(CF3)10 with diethyl malonate and CBr4 in the presence of bases yields the C70(CF3)10[C(CO2Et)2] cycloadduct as a major product, along with two C70(CF3)10[CH(CO2Et)] isomers. An XRD study of the main compound demonstrates that a [2 + 1] cycloaddition occurs at the unoccupied pole of the p7mp-C70(CF3)10 molecule. The observed regiochemical selectivity of the [2 + 1] cycloaddition is shown to be favored from both energetic and orbital reactivity viewpoints.

Graphical abstract: Regioselective synthesis and crystal structure of C70(CF3)10[C(CO2Et)2]

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Article information

DOI
https://doi.org/10.1039/B704924B
Article type
Paper
Submitted
03 Apr 2007
Accepted
08 Aug 2007
First published
28 Aug 2007

New J. Chem., 2008,32, 89-93

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Regioselective synthesis and crystal structure of C70(CF3)10[C(CO2Et)2]

N. S. Ovchinnikova, D. V. Ignat’eva, N. B. Tamm, S. M. Avdoshenko, A. A. Goryunkov, I. N. Ioffe, V. Yu. Markov, S. I. Troyanov, L. N. Sidorov, M. A. Yurovskaya and E. Kemnitz, New J. Chem., 2008, 32, 89 DOI: 10.1039/B704924B

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