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Russian Journal of Organic Chemistry

, Volume 52, Issue 3, pp 299–306 | Cite as

Methyl (Z)-3-bromo-3-(4-methylbenzenesulfonyl)prop-2-enoate: Synthesis and reactions with dimethyl malonate and methyl acetoacetate

  • V. A. Vasin
  • I. Yu. Bolusheva
  • V. V. Razin
  • S. R. Kapkaeva
  • P. S. Petrov
  • N. V. Somov
Article

Abstract

Bromination–dehydrobromination of methyl (E)-3-(4-methylbenzenesulfonyl)prop-2-enoate gave methyl (Z)-3-bromo-3-(4-methylbenzenesulfonyl)prop-2-enoate whose structure was determined by X-ray analysis. Methyl (Z)-3-bromo-3-(4-methylbenzenesulfonyl)prop-2-enoate behaved as a synthetic equivalent of methyl 3-(4-methylbenzenesulfonyl)prop-2-ynoate in reactions with dimethyl malonate and methyl acetoacetate, which afforded the corresponding Michael adducts, trimethyl 3-(4-methylbenzenesulfonyl)prop-1-ene-1,1,2-tricarboxylate and dimethyl (Z)-2-acetyl-3-(4-methylbenzenesulfonyl)but-2-enedioate, respectively, via nucleophilic attack on the β-position with respect to the sulfonyl group.

Keywords

Dimethyl Fumarate Methyl Acetoacetate Dimethyl Malonate Dimethyl Maleate Acetyl Carbonyl Carbon 
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.
    Vasin, V.A., Bolusheva, I.Yu., and Razin, V.V., Chem. Heterocycl. Compd., 2008, vol. 44, p. 419.CrossRefGoogle Scholar
  2. 2.
    Vasin, V.A., Bolusheva, I.Yu., and Razin, V.V., Russ. J. Org. Chem., 2012, vol. 48, p. 1173.CrossRefGoogle Scholar
  3. 3.
    Vasin, V.A., Bolusheva, I.Yu., Razin, V.V., and Somov, N.V., Russ. J. Org. Chem., 2014, vol. 50, p. 993.CrossRefGoogle Scholar
  4. 4.
    Vasin, V.A., Bolusheva, I.Yu., Kalyazin, V.A., and Razin, V.V., Russ. J. Org. Chem., 2014, vol. 50, p. 1448.CrossRefGoogle Scholar
  5. 5.
    Vasin, V.A., Razin, V.V., Bezrukova, E.V., Korovin, D.Yu., Petrov, P.S., and Somov, N.V., Russ. J. Org. Chem., 2015, vol. 51, p. 1144.CrossRefGoogle Scholar
  6. 6.
    Vasin, V.A., Bolusheva, I.Yu., Masterova, Yu.Yu., and Razin, V.V., Russ. J. Org. Chem., 2011, vol. 47, p. 1139.CrossRefGoogle Scholar
  7. 7.
    Günther, H., NMR Spectroscopy: An Introduction, Chichester Wiley, 1980. Translated under the title Vvedenie v kurs spektroskopii YaMR, Moscow: Mir, 1984, chap. IV, p. 114.Google Scholar
  8. 8.
    Hadden, C.E., Martin, G.E., and Krishnamurthy, V.V., Magn. Reson. Chem., 2000, vol. 38, p. 143.CrossRefGoogle Scholar
  9. 9.
    Whitesell, J.K. and Minton, M.A., Stereochemical Analysis of Alicyclic Compounds by C-13 NMR Spectroscopy, New York Chapman and Hall, 1987.CrossRefGoogle Scholar
  10. 10.
    Rajakumar, P. and Kannan, A., J. Chem. Soc., Chem. Commun., 1989, p. 154.Google Scholar
  11. 11.
    MarvinBeans 15.11.16.0. http://wwwchemaxoncom/Google Scholar
  12. 12.
    Perdew, J.P., Burke, K., and Ernzerhof, M., Phys. Rev. Lett., 1996, vol. 77, p. 3865.CrossRefGoogle Scholar
  13. 13.
    Laikov, D.N., Chem. Phys. Lett., 2005, vol. 416, p. 116.CrossRefGoogle Scholar
  14. 14.
    Laikov, D.N., Chem. Phys. Lett., 1997, vol. 281, p. 151.CrossRefGoogle Scholar
  15. 15.
    CrysAlisPro, Version 1.171.37.35 (release 13-08-2014 CrysAlis171.NET), Agilent Technologies.Google Scholar
  16. 16.
    Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.CrossRefGoogle Scholar
  17. 17.
    Farrugia, L.J., J. Appl. Crystallogr., 1999, vol. 32, p. 837.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • V. A. Vasin
    • 1
  • I. Yu. Bolusheva
    • 1
  • V. V. Razin
    • 2
  • S. R. Kapkaeva
    • 1
  • P. S. Petrov
    • 1
  • N. V. Somov
    • 3
  1. 1.Ogarev Mordovian State UniversitySaranskRussia
  2. 2.St. Petersburg State UniversitySt. PetersburgRussia
  3. 3.Lobachevskii State University of Nizhny NovgorodNizhny NovgorodRussia

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