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Russian Journal of Organic Chemistry

, Volume 48, Issue 4, pp 519–522 | Cite as

Convenient synthesis of α-bromo ketones by the Meerwein reaction

  • Yu. V. Ostapiuk
  • V. S. Matiichuk
  • N. I. Pidlypnyi
  • N. D. ObushakEmail author
Article

Abstract

A simple and convenient procedure was proposed for the synthesis of 4-aryl-3-bromobutan-2-ones from methyl vinyl ketone and arenediazonium bromides under Meerwein reaction conditions.

Keywords

Reaction Temperature Aromatic Amine Sodium Nitrite Diazonium Salt Benzenesulfonamide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Larock, R.C., Comprehensive Organic Transformations: A Guide to Functional Group Preparations, New York: Wiley, 1999, 2nd ed., p. 715; De Kimpe, N. and Verhé, R., The Chemistry of α-Haloketones, α-Haloaldehydes, and α-Haloimines, Patai, S. and Rappoport, Z., Eds., Chichester: Wiley, 1988, p. 1; Erian, A.W., Sherif, S.M., and Gaber, H.M., Molecules, 2003, vol. 8, p. 793; Moiseev, I.K., Zemtsova, M.N., and Makarova, N.V., Khim. Geterotsikl. Soedin., 1994, p. 867.Google Scholar
  2. 2.
    Lawton, G.R., Ji, H., Martásek, P., Roman, L.J., Silverman, R.B., Beilstein J. Org. Chem., 2009, vol. 5, article no. 28; Schwarz, O., Jakupovic, S., Ambrosi, H.-D., Haustedt, L.O., Mang, C., and Müller-Kuhrt, L., J. Comb. Chem., 2007, vol. 9, p. 1104.Google Scholar
  3. 3.
    Ke, X., Hu, H., Zhang, K., Xu, W., Zhu, Q., Wu, L., and Hu, X., Chem. Commun., 2009, p. 1037.Google Scholar
  4. 4.
    Pavlinac, J., Zupan, M., Laali, K.K., and Stavber, S., Tetrahedron, 2009, vol. 65, p. 5625.CrossRefGoogle Scholar
  5. 5.
    Kirihara, M., Ogawa, S., Noguchi, T., Okubo, K., Monma, Y., Shimizu, I., Shimosaki, R., Hatano, A., and Hirai, Y., Synlett, 2006, p. 2287; Khan, A.T., Ali, M.A., Goswami, P., and Choudhury, L.H., J. Org. Chem., 2006, vol. 71, p. 8961; Chen, J.-M. and Huang, X., Synthesis, 2004, p. 1577.Google Scholar
  6. 6.
    Heinrich, M.R., Chem. Eur. J., 2009, vol. 15, p. 820.CrossRefGoogle Scholar
  7. 7.
    Rondestvedt, C.S., Jr., Organic Reactions, Dauben, W.G., Ed., New York: Wiley, 1976, vol. 24, p. 225; Dombrovskii, A.V., Usp. Khim., 1984, vol. 53, p. 1625; Rondestvedt, C.S., Organic Reactions, Cope, A.C., Ed., New York: Wiley, 1960, vol. 11. Translated under the title Organicheskie reaktsii, Moscow: Mir, 1965, vol. 11, p. 199.Google Scholar
  8. 8.
    Obushak, M.D., Lyakhovych, M.B., and Ganushchak, M.I., Tetrahedron Lett., 1998, vol. 39, p. 9567; Obushak, N.D., Lyakhovich, M.B., and Bilaya, E.E., Russ. J. Org. Chem., 2002, vol. 38, p. 38.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2012

Authors and Affiliations

  • Yu. V. Ostapiuk
    • 1
  • V. S. Matiichuk
    • 1
  • N. I. Pidlypnyi
    • 1
  • N. D. Obushak
    • 1
    Email author
  1. 1.Ivan Franko National University of LvivLvivUkraine

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