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Retro-Bingel reaction in the electrochemical reduction of bis(dialkoxyphosphoryl)methanofullerenes

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Abstract

Four steps of reduction were detected for bis(diethoxyphosphoryl)- and bis(diisopropoxyphosphoryl)methano[60]fullerenes (1, 2) and bis(diethoxyphosphoryl)methano[70]fullerene (3) by cyclic voltammetry in the o-dichlorobenzene—DMF (3 : 1, v/v)/Bu4NBF4 (0.1 mol L–1) system on a glass-carbon electrode. At the first step the reversible transfer of one electron affords stable radical anions 1 and 2 (g = 1.9999, ΔH = 1.9 G). When two electrons per molecule are transferred, the methano fragment is rapidly eliminated (retro-Bingel reaction). This process involves the step-by-step cleavage of two C—C bonds of exo-carbon with the fullerene shell in combination with the stepwise transfer of other two electrons and a proton to form finally the carbanion of the methano fragment and fullerene dianion. For all studied compounds, the elimination rate is much higher than that for bis(alkoxycarbonyl)- and dialkoxyphosphoryl(alkoxycarbonyl)methano[60]fullerenes, which makes it possible to propose bisphosphorylmethane groups as protective in synthesis of new fullerene derivatives.

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Authors and Affiliations

  1. Kazan Scientific Center of the Russian Academy of Sciences, A. E. Arbuzov Institute of Organic and Physical Chemistry, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    V. V. Yanilkin, N. V. Nastapova, V. P. Gubskaya, V. I. Morozov, L. Sh. Berezhnaya & I. A. Nuretdinov

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  1. V. V. Yanilkin
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  2. N. V. Nastapova
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  3. V. P. Gubskaya
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  4. V. I. Morozov
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  5. L. Sh. Berezhnaya
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  6. I. A. Nuretdinov
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Yanilkin, V.V., Nastapova, N.V., Gubskaya, V.P. et al. Retro-Bingel reaction in the electrochemical reduction of bis(dialkoxyphosphoryl)methanofullerenes. Russian Chemical Bulletin 51, 72–77 (2002). https://doi.org/10.1023/A:1015005628871

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