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Synthesis of 1,3,4,6-tetraoxo compounds

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Abstract

The two-step method of synthesis of 1,3,4,6-tetraoxocompounds with different terminal substituents is developed. By condensation of alkyl methyl ketones with dimethyl oxalate new 1,6-dialkyl-substituted 1,3,4,6-tetraoxohexanes are obtained. The esters of 3,4,6-trioxoalkanoic acids are synthesized by the condensation reaction of alkyl acetates with dialkyl oxalates and alkyl methyl ketones. By the reaction of ethyl acetate with diethyl oxalate and methyl acetate the mixed diester of 3,4-dioxo-1,6-hexanedioic (ketipic) acid has been first prepared. Specific structural features of the synthesized compounds are discussed basing on the data of the IR, NMR, and XRD diffraction (XRD) analysis.

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Authors and Affiliations

  1. Orenburg Branch, Moscow Technological Institute, pr. Pobedy 75, Orenburg, 460018, Russia

    P. P. Mukovoz

  2. Perm State Humanitary Pedagogical University, Perm, Russia

    V. O. Koz’minykh

  3. Orenburg State University, Orenburg, Russia

    A. V. Gorbunova

  4. I.Ya. Postovskii Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences, Yekaterinburg, Russia

    P. A. Slepukhin & I. N. Ganebnykh

  5. Ural Federal University named after the first President of Russia B.N. Yeltsin, Yekaterinburg, Russia

    P. A. Slepukhin, O. S. El’tsov & I. N. Ganebnykh

  6. Institute of Solid State Physics of Russian Academy of Sciences, Chernogolovka, Russia

    A. V. Kuzmin

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  1. P. P. Mukovoz
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  2. V. O. Koz’minykh
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  3. A. V. Gorbunova
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  4. P. A. Slepukhin
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  5. O. S. El’tsov
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  6. I. N. Ganebnykh
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Correspondence to P. P. Mukovoz.

Additional information

Original Russian Text © P.P. Mukovoz, V.О. Koz’minykh, А.V. Gorbunova, P.А. Slepukhin, О.S. El’tsov, I.N. Ganebnykh, А.V. Kuzmin, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 11, pp. 1784–1793.

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Mukovoz, P.P., Koz’minykh, V.O., Gorbunova, A.V. et al. Synthesis of 1,3,4,6-tetraoxo compounds. Russ J Gen Chem 86, 2427–2436 (2016). https://doi.org/10.1134/S1070363216110050

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  • DOI: https://doi.org/10.1134/S1070363216110050

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