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β,β-Dinitrostyrenes: Specificity of synthesis and structure

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Abstract

An improved procedure was developed for the synthesis of β,β-dinitrostyrenes, which increased the yield and reproducibility and made the products more accessible from the preparative viewpoint. Complex analysis of the spectral data (IR, UV, 1H and 13C NMR) and results of quantum-chemical calculations showed that 2-aryl-1,1-dinitroethene molecules have a structure in which one nitro group resides in the C=C bond plane while the other deviates from this plane. The C=C bond in 2-aryl-1,1-dinitroethene molecules was found to possess enhanced polarization and electrophilicity as compared to the corresponding bond in model mononitrostyrenes.

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Authors and Affiliations

  1. Hertzen Russian State Pedagogical University, nab. r. Moiki 48, St. Petersburg, 191186, Russia

    V. M. Berestovitskaya, E. A. Pabolkova & E. V. Trukhin

  2. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 190013, Russia

    A. V. Belyakov

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  1. V. M. Berestovitskaya
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  2. E. A. Pabolkova
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  3. A. V. Belyakov
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  4. E. V. Trukhin
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Correspondence to V. M. Berestovitskaya.

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Original Russian Text © V.M. Berestovitskaya, E.A. Pabolkova, A.V. Belyakov, E.V. Trukhin, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77, No. 11, pp. 1859–1865.

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Berestovitskaya, V.M., Pabolkova, E.A., Belyakov, A.V. et al. β,β-Dinitrostyrenes: Specificity of synthesis and structure. Russ J Gen Chem 77, 1912–1918 (2007). https://doi.org/10.1134/S1070363207110114

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  • DOI: https://doi.org/10.1134/S1070363207110114

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