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

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.

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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

    Article  CAS  PubMed  Google 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

    Article  CAS  Google 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

    Article  CAS  Google 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

    Article  CAS  Google 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

    CAS  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

    Article  CAS  Google 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

    Article  CAS  Google 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

    Article  CAS  Google 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

    Article  CAS  Google 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

    Article  CAS  Google 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

    Article  CAS  Google Scholar 

  16. 16.

    Silverstein, R.M., Webster, F.X., and Kiemle, D., Spectrometric Identification of Organic Compounds, Wiley, 2009.

    Google Scholar 

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Correspondence to S. V. Makarenko.

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Makarenko, S.V., Pelipko, V.V., Pavchenko, M.M. et al. Alkyl 3-Bromo-3-nitroacrylates in Reactions with Aliphatic Alcohols. Russ J Gen Chem 89, 532–535 (2019). https://doi.org/10.1134/S1070363219030265

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Keywords

  • nitroacrylates
  • alcohols
  • nucleophilic addition
  • diastereomers
  • diastereotopy