Synthesis, structures, and properties of new thiophosphorylated fullerenopyrrolidines. First example of the Pishchimuka reaction in fullerene derivatives |
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| Authors: | G M Fazleeva V P Gubskaya F G Sibgatullina V V Yanilkin N V Nastapova Sh K Latypov A A Balandina I E Ismaev V V Zverev Yu Ya Efremov I A Nuretdinov |
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| Institution: | (1) A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088 Kazan, Russian Federation |
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| Abstract: | The reactions of fullerene C60 with thiophosphorylated mono-or dialdehydes and N-methylglycine in toluene afforded new thiophosphorylated fullerenopyrrolidines, including those containing the free aldehyde
group. The purity and compositions of the reaction products were confirmed by MALDI-TOF mass spectrometry and HPLC. The structures
of the reaction products were established by two-dimensional homo-and heterocorrelation NMR experi-ments. The properties of
the products were studied by cyclic voltammetry and quantum chemical methods. The Pishchimuka rearrangement in thiophosphorylated
derivatives of fullerenopyrrolidines was performed for the first time, and thiol esters of phosphonic acids of fullerenopyrrolidines
were prepared.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 489–497, March, 2006. |
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| Keywords: | fullerene C60 thiophosphorylated fullerenopyrrolidines NMR spectroscopy cyclic voltammetry MALDI-TOF mass spectrometry |
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