Reductive Hydrogenation of C s ‐C 70 (CF 3 ) 8 and C 1 ‐C 70 (CF 3 ) 10

CF 3 ‐derivatized fullerenes prove once again to be promising scaffolds for regioselective fullerene functionalization: now with the smallest possible addends—hydrogen atoms. Hydrogenation of C s ‐C 70 (CF 3 ) 8 and C 1 ‐C 70 (CF 3 ) 10 by means of reduction with Zn/Cu couple in the presence of wate...

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Published in:Chemistry, an Asian journal an Asian journal, 2016-07, Vol.11 (13), p.1945-1954
Main Authors: Brotsman, Victor A., Bogdanov, Viktor P., Rybalchenko, Alexey V., Galanicheva, Evgenia P., Belov, Nikita M., Markov, Vitaliy Yu, Lukonina, Natalia S., Ioffe, Ilya N., Troyanov, Sergey I., Kemnitz, Erhard, Goryunkov, Alexey A.
Format: Article
Language:English
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Summary:CF 3 ‐derivatized fullerenes prove once again to be promising scaffolds for regioselective fullerene functionalization: now with the smallest possible addends—hydrogen atoms. Hydrogenation of C s ‐C 70 (CF 3 ) 8 and C 1 ‐C 70 (CF 3 ) 10 by means of reduction with Zn/Cu couple in the presence of water proceeds regioselectively, yielding only one major isomer of C 70 (CF 3 ) 8 H 2 and only two for C 70 (CF 3 ) 10 H 2 , whose addition patterns are combined in the only abundant isomer of C 70 (CF 3 ) 10 H 4 . 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.
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.201600491