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Synthesis and Structure of Phosphorylated Nitronorbornenes

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Abstract

A procedure was suggested for preparing previously unknown phosphorylated nitronorbornenes from nitroethenephosphonates and cyclopentadienes. The structures of the products were studied by IR and 1H and 3 1P NMR spectroscopy. A single crystal X-ray diffraction study of bis(2-chloroethyl) 3-bromo-3-nitro- bicyclo[2.2.1]-5-heptene-2-phosphonate showed that the steric arrangement of the bicyclic fragment is typical of norbornenes. It is the endo-(NO2) diastereomer in which Br and P(O)(OC2H4Cl)2 substituents are eclipsed, and C2-C3 and C3-NO2 bonds are noticeably elongated.

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Authors and Affiliations

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

    V. M. Berestovitskaya, N. A. Anisimova, I. A. Litvinov, A. A. Kuzhaeva, G. A. Berkova, A. T. Gubaidullin & L. I. Deiko

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

    V. M. Berestovitskaya, N. A. Anisimova, I. A. Litvinov, A. A. Kuzhaeva, G. A. Berkova, A. T. Gubaidullin & L. I. Deiko

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  1. V. M. Berestovitskaya
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Berestovitskaya, V.M., Anisimova, N.A., Litvinov, I.A. et al. Synthesis and Structure of Phosphorylated Nitronorbornenes. Russian Journal of General Chemistry 74, 523–529 (2004). https://doi.org/10.1023/B:RUGC.0000031850.60693.3a

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  • DOI: https://doi.org/10.1023/B:RUGC.0000031850.60693.3a

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