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Hydrolysis of 6,6-dimethyl-4,8-dioxo-5,7-dioxaspiro[2.5]octane-1,1,2,2-tetracarbonitrile

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Abstract

Hydrolysis of 6,6-dimethyl-4,8-dioxo-5,7-dioxaspiro[2.5]octane-1,1,2,2-tetracarbonitrile in aqueous dioxane in the presence of hydrogen bromide gave a mixture of 2,2,3,3-tetracyanocyclopropane-1-carboxylic acid and ammonium 3-cyano-4-dicyanomethylidene-5-oxo-4,5-dihydro-1H-pyrrol-2-olate. Hydrolysis of the same compound in the presence of sulfuric acid was accompanied by nitrogen migration and led to the formation of (1R*,2S*,3S*)-1,3-dicyanocyclopropane-1,2-dicarboxamide whose structure was proved by X-ray analysis.

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Authors and Affiliations

  1. I.N. Ul’yanov Chuvash State University, Moskovskii pr. 15, Cheboskary, 428015, Russia

    O. V. Kayukova, I. N. Bardasov, Ya. S. Kayukov, O. V. Ershov, A. V. Eremkin & O. E. Nasakin

  2. Moscow State University, Vorob’evy gory 1, Moscow, 119992, Russia

    V. A. Tafeenko

Authors
  1. O. V. Kayukova
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  2. I. N. Bardasov
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  3. Ya. S. Kayukov
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  4. O. V. Ershov
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  5. A. V. Eremkin
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  6. O. E. Nasakin
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  7. V. A. Tafeenko
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Corresponding author

Correspondence to O. V. Kayukova.

Additional information

Original Russian Text © O.V. Kayukova, I.N. Bardasov, Ya.S. Kayukov, O.V. Ershov, A.V. Eremkin, O.E. Nasakin, V.A. Tafeenko, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 12, pp. 1837–1840.

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Kayukova, O.V., Bardasov, I.N., Kayukov, Y.S. et al. Hydrolysis of 6,6-dimethyl-4,8-dioxo-5,7-dioxaspiro[2.5]octane-1,1,2,2-tetracarbonitrile. Russ J Org Chem 43, 1842–1845 (2007). https://doi.org/10.1134/S1070428007120184

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  • DOI: https://doi.org/10.1134/S1070428007120184

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