Advertisement

Russian Journal of General Chemistry

, Volume 89, Issue 3, pp 532–535 | Cite as

Alkyl 3-Bromo-3-nitroacrylates in Reactions with Aliphatic Alcohols

  • S. V. MakarenkoEmail author
  • V. V. Pelipko
  • M. M. Pavchenko
  • R. I. Baichurin
Letters to the Editor
  • 14 Downloads

Abstract

The reactions of alkyl 3-bromo-3-nitroacrylates with aliphatic alcohols at reflux led to the formation of O-adducts—alkyl 2-alkoxy-3-bromo-3-nitropropanoates isolated as mixtures of diastereomers; their structure was proved using 1H, 13C-{1H} NMR, and IR spectroscopy methods.

Keywords

nitroacrylates alcohols nucleophilic addition diastereomers diastereotopy 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Perekalin, V.V., Lipina, E.S., Berestovitskaya, V.M., and Efremov, D.A., Nitroalkenes. Conjgated Nitrocompounds, Chichester: John Wiley and Sons, 1994.Google Scholar
  2. 2.
    Soengas, R.G., Acúrcio, R.C., and Silva, A.M.S., Eur. J. Org. Chem., 2014, no. 29, p. 6339. doi  https://doi.org/10.1002/ejoc.201402043
  3. 3.
    Soengas, R.G., Rodríguez-Solla, H., Silva, A.M.S., Llavona, R., and Paz, F.A.A., J. Org. Chem., 2013, vol. 78, no. 24, p. 12831. doi  https://doi.org/10.1021/jo4021634 CrossRefPubMedGoogle Scholar
  4. 4.
    Berestovitskaya, V.M., Ozerova, O.Yu., Efimova, T.P., Gurzhiy, V.V., and Novikova, T.A., Mendeleev Commun., 2016, vol. 26, no. 4, p. 323. doi  https://doi.org/10.1016/j.mencom.2016.07.019 CrossRefGoogle Scholar
  5. 5.
    Makarenko, S.V., Sadykov, K.D., and Baichurin, R.I., Chem. Heterocycl. Compd., 2018, vol. 54, no. 5, p. 502. doi  https://doi.org/10.1007/s10593-018-2296-9 CrossRefGoogle Scholar
  6. 6.
    Makarenko, S.V., Baichurin, R.I., Gurzhiy, V.V., and Baichurina, L.V., Russ. Chem. Bull., 2018, vol. 67, no. 5, p. 815. doi  https://doi.org/10.1007/s11172-013-0196-9 CrossRefGoogle Scholar
  7. 7.
    Baiju, T.V., Almeida, R.G., Sivanandan, S.T., de Simone, C.A., Brito, L.M., Cavalcanti, B.C., Pessoa, C., Namboothiri, I.N.N., and da Silva Júnior, E.N., Med. Chem., 2018, vol. 151, p. 686. doi  https://doi.org/10.1016/j.ejmech.2018.03.079 Google Scholar
  8. 8.
    Zhang, J.-W., Yu, L.-S.-H., Dong, J.-L., Sun, Q.-C., and Xie, J.-W., Synlett, 2018, vol. 29, no. 5, p. 603. doi  https://doi.org/10.1055/s-0036-1591838 CrossRefGoogle Scholar
  9. 9.
    Loevenich, J., Koch, J., and Pucknat, U., Ber., 1930, vol. 63, no. 3, p. 636. doi  https://doi.org/10.1002/cber.19300630316 Google Scholar
  10. 10.
    Reichert, B. and Koch, W., Ber., 1935, vol. 68, no. 3, p. 445. doi  https://doi.org/10.1002/cber.19350680315 Google Scholar
  11. 11.
    Yamamura, K., Watarai, S., and Kinugasa, T., Bull. Chem. Soc. Japan, 1971, vol. 44, no. 9, p. 2440. doi  https://doi.org/10.1246/bcsj.44.2440 CrossRefGoogle Scholar
  12. 12.
    Shiga, M., Tsunashima, M., Kono, H., Motoyama, I., and Hata, K., Bull. Chem. Soc. Japan, 1970, vol. 43, no. 3, p. 841. doi  https://doi.org/10.1246/bcsj.43.841 CrossRefGoogle Scholar
  13. 13.
    Stukan’, E.V., Makarenko, S.V., Berkova, G.A., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2010, vol. 80, no. 12, p. 2460. doi  https://doi.org/10.1134/S1070363210120108 CrossRefGoogle Scholar
  14. 14.
    Sarkisyan, Z.M., Sadikov, K.D., Smirnov, A.S., Kuzhaeva, A.A., Makarenko, S.V., Anisimova, N.A., Deiko, L.I., and Berestovitskaya, V.M., Russ. J. Org. Chem., 2004, vol. 40, no. 6, p. 908. doi  https://doi.org/10.1023/B:RUJO.0000044559.83690.b4 CrossRefGoogle Scholar
  15. 15.
    Anderson, J.C., Kalogirou, A.S., and Tizzard, G.J., Tetrahedron, 2014, vol. 70, no. 49, p. 9337. doi  https://doi.org/10.1016/j.tet.2014.10.042 CrossRefGoogle Scholar
  16. 16.
    Silverstein, R.M., Webster, F.X., and Kiemle, D., Spectrometric Identification of Organic Compounds, Wiley, 2009.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • S. V. Makarenko
    • 1
    Email author
  • V. V. Pelipko
    • 1
  • M. M. Pavchenko
    • 1
  • R. I. Baichurin
    • 1
  1. 1.Herzen State PedagogicalUniversity of RussiaSt. PetersburgRussia

Personalised recommendations