Regioselective synthesis and crystal structure of C70(CF3)10[C(CO2Et)2]†
Nataliya S. Ovchinnikova,Daria V. Ignat’eva,Nadezhda B. Tamm,Stanislav M. Avdoshenko,Alexey A. Goryunkov,Ilya N. Ioffe,Vitaliy Yu. Markov,Sergey I. Troyanov,Lev N. Sidorov,Marina A. Yurovskaya,Erhard Kemnitz
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]](http://hg.y866.cn/compound/lib/scimg/usr/1/B704924B.jpg)
