Skip to main content
SpringerLink
Log in

Synthesis and structure of alkyl-α-arylamino-β-bromo-β-nitroacrylates, new functionalized β-nitroenamines

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

New bromonitroenamine compounds, alkyl-2-arylamino-3-bromo-3-nitroacrylates, were synthesized and characterized using IR, UV, 1H and 13C NMR spectroscopy, and X-ray analysis. Their molecules were found to have the E-configuration and to exist as highly conjugated structures. According to the X-ray analysis, in the ethyl-3-bromo-2-(p-bromophenylamino)-3-nitroacrylate molecule the bromonitroenamine moiety is almost planar, the ester group is located completely out of the C=C double bond plane, amino hydrogen and nitro oxygen atoms form an intramolecular hydrogen bond.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Rajappa, S., Tetrahedron, 1999, vol. 55, no. 8, p. 7065.

    Article  CAS  Google Scholar 

  2. Tokumitsu, T. and Hayashi, T., J. Org. Chem., 1985, vol. 50, no. 9, p. 1547.

    Article  CAS  Google Scholar 

  3. Dauzonne, D., Fleurant, A., Demerseman, P., Cotrait, M., and Bideau, J.-P., Synth. Commun., 1990, vol. 20, no. 21, p. 3339.

    Article  CAS  Google Scholar 

  4. Gais, H.-J., Hafner, K., and Neuenschwander, M., Helv. Chim. Acta, 1969, vol. 52, no. 8, p. 2641.

    Article  CAS  Google Scholar 

  5. Makarenko, S.V., Trukhin, E.V., MacMillan, J., and Berestovitskaya, V.M., Zh. Org. Khim., 1999, vol. 35, no. 2, p. 330.

    Google Scholar 

  6. Ishmaeva, E.A., Berestovitskaya, V.M., Litvinov, I.A., Vereshchagina, Ya.A., Yarkova, E.G., Fattakhova, G.R., Krivolapov, D.B., Makarenko, S.V., Trukhin, E.V., and Pavlova, I.V., Zh. Obshch. Khim., 2001, vol. 71, no. 3, p. 466.

    Google Scholar 

  7. Horne, C.A., Jr., USA Patent no. 3950530, 1976, http://patft.uspto.gov/netahtml/PTO/srchnum.htm.

  8. Patent WO 2004/057960, 2004, http://ep.espacenet.com/numberSearch?locale=en_EP.

  9. Bunnange, M.E., Ganesh, Th., Masesane, Ishm, B., Orton, D., and Steel, P.G., Org. Lett., 2003, vol. 5, no. 3, p. 239.

    Article  Google Scholar 

  10. Stork, G., Tang, P.C., Casey, M., Goodman, B., and Touota, M., J. Am. Chem. Soc., 2005, vol. 127, no. 46, p. 16255.

    Article  CAS  Google Scholar 

  11. Rimkus, A. and Sewald, N., Org. Lett., 2003, vol. 5, no. 1, p. 79.

    Article  CAS  Google Scholar 

  12. Cheng, R.P., Gellman, S.H., and DeGrado, W.F., Chem. Rev., 2001, vol. 101, no. 10, p. 3219.

    Article  CAS  Google Scholar 

  13. Makarenko, S.V., Kovalenko, K.S., Krivolapov, D.B., Litvinov, I.A., and Berestovitskaya, V.M., Izv. Akad. Nauk, Ser. Khim., 2009, no. 10, p. 1977.

  14. Meyer, C., Zapol’skii, V.A., Adam, A.E.W., and Kaufmann, D.E., Synthesis, 2008, no. 16, p. 2575.

  15. Paperno, T.Ya. and Perekalin, V.V., Infrakrasnye spektry nitrosoedinenii (IR Spectra of Nitro Compounds), Leningrad, LGPI, 1974.

    Google Scholar 

  16. Pretsch, E., Büllmann, P., and Affolter, C., Structure Determination of Organic Compounds. Tables of Spectral Data, Berlin: Springer, 2000.

    Google Scholar 

  17. Paperno, T.Ya., Perekalin, V.V., and Sopova, A.S., Zh. Prikl. Spektr., 1973, vol. 19, no. 4, p. 649.

    CAS  Google Scholar 

  18. Sadikov, K.D., Candidate Sci. (Chem.) Dissertation, St. Petersburg, 2005.

  19. Hess, H.D., Bauder, A., and Gainthard, H.H., J. Mol. Spectr., 1967, vol. 22, no. 2, p. 208.

    Article  CAS  Google Scholar 

  20. Andrianov, V.G., Struchkov, Yu.T., and Babievsky, K.K., Cryst. Struct. Commun., 1982, no. 11, p. 31.

  21. Berestovitskaya, V.M., Bundule, M.F., Bleidelis, Ya.Ya., and Efremova, I.E., Zh. Obshch. Khim., 1986, vol. 56, no. 2, p. 375.

    CAS  Google Scholar 

  22. Sheldrick, G.M., SADABS, 1998, 2.01, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA.

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

    Article  Google Scholar 

  24. Sheldrick, G.M., SADABS, Program for empirical X-Ray Absorption Correction, Bruker-Nonius, 1990–2004.

  25. Farrugia, L.J., J. Appl. Crystal., 1999, vol. 32, p. 837.

    Article  CAS  Google Scholar 

  26. APEX2 (Version 2.1), SAINTPlus, Data Reduction and Correction Program (Version 7.31A, Bruker Advansed X-ray Solutions, BrukerAXS Inc., Madison, Wisconsin, USA, 2006.

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

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    V. M. Berestovitskaya, S. V. Makarenko, K. S. Kovalenko & A. D. Shevchenko

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

    I. A. Litvinov & D. B. Krivolapov

Authors
  1. V. M. Berestovitskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. V. Makarenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. S. Kovalenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. A. Litvinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. D. B. Krivolapov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. D. Shevchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to K. S. Kovalenko.

Additional information

Original Russian Text © V.M. Berestovitskaya, S.V. Makarenko, K.S. Kovalenko, I.A. Litvinov, D.B. Krivolapov, A.D. Shevchenko, 2011, published in Zhurnal Obshchei Khimii, 2011, Vol. 81, No. 2, pp. 277–286.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Berestovitskaya, V.M., Makarenko, S.V., Kovalenko, K.S. et al. Synthesis and structure of alkyl-α-arylamino-β-bromo-β-nitroacrylates, new functionalized β-nitroenamines. Russ J Gen Chem 81, 376–384 (2011). https://doi.org/10.1134/S1070363211020162

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363211020162

Keywords

Search

Navigation