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Reaction of bis(2-chloroethyl)-2-nitroethynylphosphonate with diazoacetic ester

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Abstract

Reactions of 1,3-dipolar cycloaddition of bis(2-chloroethyl)-2-nitroethenylphosphonate to methyl and ethyl diazoacetates proceed with the formation of a mixture of regioisomers of phosphorylated nitropyrazoline carboxylates that under the reaction conditions undergo isomeric transformations and denitration and afford a mixture of Δ1- and Δ2-pyrazoline- and pyrazolecarboxylates. Structures of the synthesized substances are studied by the methods of IR and 1H, 31P NMR spectroscopy and partially by X-ray structural analysis.

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References

  1. Deiko, L.I., Botata, Zh.E., Paperno, T.Ya., and Berestovitskaya, V.M., Zh. Obshch. Khim., 1995, vol. 65, no. 6, p. 1052.

    CAS  Google Scholar 

  2. Berestovitskaya, V.M., Deiko, L.I., Botata, Zh.E., and Berkova, G.A., Zh. Obshch. Khim., 1998, vol. 68, no. 1, p. 160.

    Google Scholar 

  3. Kuzhaeva, A.A., Berestovitskaya, V.M., Deiko, L.I., Anisimova, N.A., and Berkova, G.A., Zh. Obshch. Khim., 2002, vol. 72, no. 10, p. 1752.

    Google Scholar 

  4. Berestovitskaya, V.M., Anisimova, N.A., Kuzhaeva, A.A., Berkova, G.A., and Deiko, L.I., Zh. Obshch. Khim., 2007, vol. 77, no. 1, p. 29.

    Google Scholar 

  5. Kuzhaeva, A.A., Anisimova, N.A., Deiko, L.I., Berkova, G.A., and Berestovitskaya, V.M., Khim. Geterotsikl. Soed., 2003, no. 8, p. 1264.

  6. Berestovitskaya, V.M., Anisimova, N.A., Litvinov, I.A., Kuzhaeva, A.A., Berkova, G.A., Gubaidullin, A.T., and Deiko, L.I., Zh. Obshch. Khim., 2004, vol. 74, no. 4, p. 574.

    Google Scholar 

  7. Anisimova, N.A., Kuzhaeva, A.A., Berkova, G.A., Deiko, L.I., and Berestovitskaya, V.M., Zh. Obshch. Khim., 2005, vol. 75, no. 7, p. 1106.

    Google Scholar 

  8. Anisimova, N.A., Kuzhaeva, A.A., Berkova, G.A., Deiko, L.I., and Berestovitskaya, V.M., Zh. Obshch. Khim., 2005, vol. 75, no. 5, p. 729.

    Google Scholar 

  9. Makarova, N.G., Anisimova, N.A., Berkova, G.A., Deiko, L.I., and Berestovitskaya, V.M., Zh. Obshch. Khim., 2005, vol. 75, no. 9, p. 1570.

    Google Scholar 

  10. Anisimova, N.A., Makarova, N.G., Berkova, G.A., and Berestovitskaya, V.M., Zh. Obshch. Khim., 2006, vol. 76, no. 10, p. 1612.

    Google Scholar 

  11. Berkova, G.A., Anisimova, N.A., Makarova, N.G., Deiko, L.I., and Berestovitskaya, V.M., Zh. Obshch. Khim., 2006, vol. 76, no. 1, p. 156.

    Google Scholar 

  12. Khusainova, N.G. and Pudovik, A.A., Usp. Khim., 1978, vol. 67, no. 9, p. 1502.

    Google Scholar 

  13. Pudovik, A.N., Gareev, R.D., and Aganov, A.V., Zh. Obshch. Khim., 1971, vol. 41, no. 5, p. 1017.

    CAS  Google Scholar 

  14. Samitov, Yu.Yu., Gareev, R.D., Stabrovskaya, L.A., and Pudovik, A.N., Zh. Obshch. Khim., 1972, vol. 42, no. 6, p. 1227.

    CAS  Google Scholar 

  15. Pudovik, A.N., Gareev, R.D., Stabrovskaya, L.A., Aganov, A.V., and Raevskaya, O.E., Zh. Obshch. Khim., 1970, vol. 40, no. 10, p. 2181.

    CAS  Google Scholar 

  16. Pudovik, A.N., Gareev, R.D., Stabrovskaya, L.A., Evstaf’ev, G.I., and Remizov, A.B., Zh. Obshch. Khim., 1973, vol. 43, no. 43, p. 1674.

    CAS  Google Scholar 

  17. Parcham, W. and Bleasdale, I.L., J. Am. Chem. Soc., 1950, vol. 72, no. 9, p. 3843.

    Article  Google Scholar 

  18. Cook., L., USA Patent no. 3.017.326, January 16, 1962. Appl. June 4, 1959.

  19. Verbruggen, R. and Viehe, H.G., Chimia, 1975, vol. 29, no. 8, p. 350.

    CAS  Google Scholar 

  20. Yanovskaya, L.A., Sovremennye teoreticheskie osnovy organicheskoi khimii (Modern Theoretical Basucity of Organic Chemistry), Moscow: Khimiya, 1978.

    Google Scholar 

  21. Gilchrist, T.L and Storr, R.C., Organicheskie reaktsii i orbital’naya simmetriya (Organic Reactions and Orbital Symmetry), Moscow: Mir, 1976.

    Google Scholar 

  22. Zbiral, E. and Bauer, E., Tetrahedron, 1972, vol. 25, no. 15, p. 4189.

    Article  Google Scholar 

  23. Doyle, M.P., Colsman, M.R., and Dorow Rh., J. Heterocycl. Chem., 1983, no. 20, p. 943.

  24. Ionin, B.I., Ershov, B.A., and Kol’tsov, A.I., YaMR spektroskopiya v organicheskoi khimii (NMR Spectroscopy in Organic Chemistry), Leningrad: Khimiya, 1983.

    Google Scholar 

  25. Elguero, J., Jacquier, R., HangCung, N., and Tien Duc., Bull. Soc. Chim. Fr., 1966, vol. 12, p. 3727.

    Google Scholar 

  26. Altomare, A., Cascarano, G., Giacovazzo, C., and Viterbo, D., Acta Crystallogr., A, 1991, vol. 47, p. 744.

    Article  Google Scholar 

  27. Sheldrick, G.M., SHELX-97. Programs for Crystal Structure Analysis (Release 97-2), University of Gottingen, Germany, 1997.

    Google Scholar 

  28. Straver, L.H. and Schierbeek, A.J., MolEN. Structure Determination System, vol. 1: Program Description, Delft: Nonius, B.V., 1994.

    Google Scholar 

  29. Farrugia, L.J., J. Appl. Cryst., 1999, vol. 32, p. 837.

    Article  Google Scholar 

  30. Spek, A.L., Acta Crystallogr., 1990, vol. 46, p. 34.

    Google Scholar 

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Authors and Affiliations

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

    V. M. Berestovitskaya, N. A. Anisimova, G. A. Berkova & N. G. Makarova

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia

    A. T. Gubaidullin & I. A. Litvinov

Authors
  1. V. M. Berestovitskaya
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  2. N. A. Anisimova
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  3. A. T. Gubaidullin
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  4. I. A. Litvinov
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  5. G. A. Berkova
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  6. N. G. Makarova
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Corresponding author

Correspondence to V. M. Berestovitskaya.

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Original Russian Text © V.M. Berestovitskaya, N.A. Anisimova, A.T. Gubaidullin, I.A. Litvinov, G.A. Berkova, N.G. Makarova, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 7, pp. 1090–1100.

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Berestovitskaya, V.M., Anisimova, N.A., Gubaidullin, A.T. et al. Reaction of bis(2-chloroethyl)-2-nitroethynylphosphonate with diazoacetic ester. Russ J Gen Chem 79, 1446–1457 (2009). https://doi.org/10.1134/S107036320907007X

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  • DOI: https://doi.org/10.1134/S107036320907007X

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