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Synthesis, structure and complexation of the fluorinated 1,3-enaminoketones containing at the nitrogen atom substituents with a terminal C≡C bond

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Abstract

The reaction of fluorinated lithium 1,3-diketonates with propargylamine hydrochloride and 1,1,1-trifluorpentane-2,4-dione or 1,1,1-trifluoro-4-methoxypent-3-en-2-one with propargylamine and 3-aminophenylacetylene were performed to obtain fluorinated 1,3-enaminones containing at a nitrogen atom substituents with terminal C≡C bonds: (Z)-1,1,1-trifluoro-4-(2-propynylamino)-3-pentene-2-one, (Z)-1,1,2,2-tetrafluoro-5-(2-propynylamino)-4-hexen-3-one, and 4-(3-ethynylphenylamino)-1,1,1-trifluoropentyl-3-en-2-one. Reactions of 4-(3-ethynyl-phenylamino)-1,1,1-trifluoro-pentyl-3-en-2-one with Cu(II) acetate or nanosized powder of copper or its oxides led to the respective chelate complex. The structure of (Z)-1,1,2,2-tetrafluoro-5-(2-propynylamino)-4-hexen-3-one and a copper complex of 4-(3-etinilphenylamino)-1,1,1-trifluoropenta-3-en-2-one was determined by XRD.

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Authors and Affiliations

  1. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, ul. S. Kovalevskoi/Academicheskaya 22/20, Yekaterinburg, 620041, Russia

    E. F. Zhilina, P. A. Slepukhin, N. S. Boltacheva, M. G. Pervova, D. L. Chizhov, V. I. Filyakova & V. N. Charushin

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  1. E. F. Zhilina
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  2. P. A. Slepukhin
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  3. N. S. Boltacheva
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  4. M. G. Pervova
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  5. D. L. Chizhov
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  6. V. I. Filyakova
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  7. V. N. Charushin
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Corresponding author

Correspondence to V. I. Filyakova.

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Original Russian Text © E.F. Zhilina, P.A. Slepukhin, N.S. Boltacheva, M.G. Pervova, D.L. Chizhov, V.I. Filyakova, V.N. Charushin, 2012, published in Zhurnal Obshchei Khimii, 2012, Vol. 82, No. 12, pp. 2008–2015.

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Zhilina, E.F., Slepukhin, P.A., Boltacheva, N.S. et al. Synthesis, structure and complexation of the fluorinated 1,3-enaminoketones containing at the nitrogen atom substituents with a terminal C≡C bond. Russ J Gen Chem 82, 1962–1969 (2012). https://doi.org/10.1134/S1070363212120092

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  • DOI: https://doi.org/10.1134/S1070363212120092

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