Stepwise Regioselective Hydrogenation of cis‐2‐C60(CF2)2 Homofullerene with [6,6]‐Open/Closed Valence Tautomerism |
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| Authors: | Viktor P Bogdanov Olesya O Semivrazhskaya Nikita M Belov Prof?Dr Sergey I Troyanov Dr Vitaliy Yu Markov Dr Ilya N Ioffe Prof?Dr Erhard Kemnitz Dr Alexey A Goryunkov |
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| Institution: | 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: | The homofullerene compound cis‐2‐C60(CF2)2, which has an unusual kind of open/closed valence tautomerism undergoes consecutive regioselective hydrogenation at bridgehead carbon atoms upon reduction with Zn/Cu couple in H2O‐toluene mixture. The tautomerism barrier in cis‐2‐C60(CF2)2 is negligible in the neutral state, whereas negative charging both impedes tautomeric transformation and promotes regioselective addition of electrophilic species at the bridgehead carbon atoms. In light of this observation, two novel homofullerene derivatives, mixed 6,6]‐open/closed C60(CF2)2H2 and 6,6]‐open cis‐2‐C60(CF2)2H4, were synthesized and their structures were unambiguously determined by means of single crystal X‐ray crystallography and NMR spectroscopy. |
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| Keywords: | fullerenes hydrogenation regioselectivity structure elucidation tautomerism |
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