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.
This is a preview of subscription content, log in to check access.
References
- 1.
Perekalin, V.V., Lipina, E.S., Berestovitskaya, V.M., and Efremov, D.A., Nitroalkenes. Conjgated Nitrocompounds, Chichester: John Wiley and Sons, 1994.
- 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.
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
- 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
- 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
- 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
- 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
- 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
- 9.
Loevenich, J., Koch, J., and Pucknat, U., Ber., 1930, vol. 63, no. 3, p. 636. doi https://doi.org/10.1002/cber.19300630316
- 10.
Reichert, B. and Koch, W., Ber., 1935, vol. 68, no. 3, p. 445. doi https://doi.org/10.1002/cber.19350680315
- 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
- 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
- 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
- 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
- 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
- 16.
Silverstein, R.M., Webster, F.X., and Kiemle, D., Spectrometric Identification of Organic Compounds, Wiley, 2009.
Author information
Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
Keywords
- nitroacrylates
- alcohols
- nucleophilic addition
- diastereomers
- diastereotopy