Reductive Hydrogenation of Cs‐C70(CF3)8 and C1‐C70(CF3)10 |
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| Authors: | Victor A. Brotsman Viktor P. Bogdanov Alexey V. Rybalchenko Evgenia P. Galanicheva Nikita M. Belov Dr. Vitaliy Yu. Markov Dr. Natalia S. Lukonina Dr. Ilya N. Ioffe Prof. Dr. Sergey I. Troyanov Prof. Dr. Erhard Kemnitz Dr. Alexey A. Goryunkov |
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| Affiliation: | 1. Chemistry Department, M. V. Lomonosov Moscow State University, Moscow, Russia;2. Institute of Chemistry, Humboldt University Berlin, Berlin, Germany |
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| Abstract: | CF3‐derivatized fullerenes prove once again to be promising scaffolds for regioselective fullerene functionalization: now with the smallest possible addends—hydrogen atoms. Hydrogenation of Cs‐C70(CF3)8 and C1‐C70(CF3)10 by means of reduction with Zn/Cu couple in the presence of water proceeds regioselectively, yielding only one major isomer of C70(CF3)8H2 and only two for C70(CF3)10H2, whose addition patterns are combined in the only abundant isomer of C70(CF3)10H4. The observed selectivity is governed by the electronic structure of trifluoromethylated substrates. Interestingly, we discovered that Clar's theory can be utilized to predict the regiochemistry of functionalization, and we look forward to testing it on forthcoming cases of derivatization of pre‐functionalized fullerene building blocks. |
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| Keywords: | Clar's sextets rule fullerenes hydrogenation regioselectivity structure elucidation |
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