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Reactions of some cyclic ketene acetals with maleic anhydride and acrylonitrile

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Abstract

The reactions of 9-methyl-4-methylidene-3,5-dioxabicyclo[5.4.0]undecane with maleic anhydride and acrylonitrile were studied by NMR spectroscopy and were found to give 1:1 molecular complexes with equilibrium constants of 0.24±0.06 and 0.14±0.04 l mol−1, respectively. Analysis of the calculated (AM1) heats of formation ΔH, differences in the dipole moments Δμ, frequencies and intensities of stretching vibrations of the donor and acceptors, and charge distribution showed formation of π-π, mixed π-π-H, and H complexes with partial charge transfer. These complexes can be used in copolymerization of the above monomers.

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Authors and Affiliations

  1. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, ul. R. Lyuksemburg 70, Donetsk, 83114, Ukraine

    V. V. Zaitseva, T. G. Tyurina & A. V. Farafonova

  2. Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia

    S. Yu. Zaitsev

Authors
  1. V. V. Zaitseva
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  2. T. G. Tyurina
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  3. A. V. Farafonova
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  4. S. Yu. Zaitsev
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Original Russian Text © V.V. Zaitseva, T.G. Tyurina, A.V. Farafonova, S.Yu. Zaitsev, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77, No. 6, pp. 961–966.

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Zaitseva, V.V., Tyurina, T.G., Farafonova, A.V. et al. Reactions of some cyclic ketene acetals with maleic anhydride and acrylonitrile. Russ J Gen Chem 77, 1049–1054 (2007). https://doi.org/10.1134/S1070363207060175

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  • DOI: https://doi.org/10.1134/S1070363207060175

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