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Indole-containing 2-Nitroethenylphosphonates: Synthesis and Structure

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Abstract

A method was developed for preparing first representatives of phosphorylated nitrovinylindoles, bis(2-chloroethyl) 1-(indol-3-yl)- and bis(2-chloroethyl) 1-(1-alkylindol-3-yl)-2-nitroethenylphosphonates, and the structures of these compounds were studied. The spectroscopic data and results of dipole moment measurements show that the molecules have E configuration with s-cis arrangement of the multiple bond and phosphoryl group. X-ray studies have shown that the molecules of the first compound, having the E-s-cis form in the solid phase also, exist in the crystal in the form of enantiomeric pairs. They are involved in inter- molecular hydrogen bonds to form infinite chains.

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Authors and Affiliations

  1. Herzen Russian State Pedagogical University, St. Petersburg, Russia

    V. M. Berestovitskaya, I. A. Litvinov, E. A. Ishmaeva, L. I. Deiko, Ya. A. Vereshchagina, Z. M. Sarkisyan, A. G. Gubaidullin, G. R. Fattakhova, S. V. Makarenko & G. A. Berkova

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Tatarstan, Russia

    V. M. Berestovitskaya, I. A. Litvinov, E. A. Ishmaeva, L. I. Deiko, Ya. A. Vereshchagina, Z. M. Sarkisyan, A. G. Gubaidullin, G. R. Fattakhova, S. V. Makarenko & G. A. Berkova

  3. Kazan State University, Kazan, Tatarstan, Russia

    V. M. Berestovitskaya, I. A. Litvinov, E. A. Ishmaeva, L. I. Deiko, Ya. A. Vereshchagina, Z. M. Sarkisyan, A. G. Gubaidullin, G. R. Fattakhova, S. V. Makarenko & G. A. Berkova

  4. Kazan State Technological University, Kazan, Tatarstan, Russia

    V. M. Berestovitskaya, I. A. Litvinov, E. A. Ishmaeva, L. I. Deiko, Ya. A. Vereshchagina, Z. M. Sarkisyan, A. G. Gubaidullin, G. R. Fattakhova, S. V. Makarenko & G. A. Berkova

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  1. V. M. Berestovitskaya
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  2. I. A. Litvinov
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  3. E. A. Ishmaeva
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  8. G. R. Fattakhova
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Berestovitskaya, V.M., Litvinov, I.A., Ishmaeva, E.A. et al. Indole-containing 2-Nitroethenylphosphonates: Synthesis and Structure. Russian Journal of General Chemistry 74, 110–119 (2004). https://doi.org/10.1023/B:RUGC.0000025178.22976.6b

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  • DOI: https://doi.org/10.1023/B:RUGC.0000025178.22976.6b

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