Advertisement

Russian Journal of Organic Chemistry

, Volume 46, Issue 3, pp 352–354 | Cite as

Cascade synthesis of new aryl 2-phenylallyl sulfones from α-methylstyrene and aromatic mono- and bis-sulfonyl chlorides

  • A. A. Pudikova
  • N. P. Gerasimova
  • Yu. A. Moskvichev
  • E. M. Alov
  • A. S. Danilova
  • O. S. Kozlova
Article

Abstract

Addition products of arenesulfonyl chlorides to α-methylstyrene in the presence of catalytic amounts of copper(II) chloride and triethylamine hydrochloride underwent fast dehydrochlorination (according to Hofmann’s rule) on heating in boiling acetonitrile to give the corresponding aryl 2-phenylallyl sulfones with high selectivity. This reaction underlay a one-pot procedure for the synthesis of new compounds that attract interest as potential biologically active substances, monomers, and cross-linking agents for polymeric materials from accessible starting compounds.

Keywords

Hydrogen Chloride Sulfonyl Chloride Vinyl Sulfone Triethylamine Hydrochloride Diphenyl Sulfone 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Asscher, M. and Vofsi, D., J. Chem. Soc., 1964, p. 4962.Google Scholar
  2. 2.
    Truce, W.E., Goralski, C.T., Christensen, L.W., and Bavry, R.H., J. Org. Chem., 1970, vol. 35, p. 4217.CrossRefGoogle Scholar
  3. 3.
    Truce, W.E. and Goralski, C.T., J. Org. Chem., 1971, vol. 36, p. 2536.CrossRefGoogle Scholar
  4. 4.
    Orochov, A., Asscher, M., and Vofsi, D., J. Chem. Soc., Perkin Trans. 2, 1973, p. 1000.Google Scholar
  5. 5.
    Inomata, K., Sasaoka, S., and Kobayashi, T., Bull. Chem. Soc. Jpn., 1987, vol. 60, p. 1767.CrossRefGoogle Scholar
  6. 6.
    Liu, L.K., Chi, Y., and Kwan-Yue Jen, J. Org. Chem., 1980, vol. 45, p. 406.CrossRefGoogle Scholar
  7. 7.
    Cristol, S.J. and Davies, D.I., J. Org. Chem., 1964, vol. 29, p. 1282.CrossRefGoogle Scholar
  8. 8.
    Konyushkin, L.D., Derzhinskii, A.R., and Prilezhaeva, E.N., Izv. Akad. Nauk SSSR, Ser. Khim., 1977, p. 938.Google Scholar
  9. 9.
    Amiel, Y., J. Org. Chem., 1971, vol. 36, p. 3691.CrossRefGoogle Scholar
  10. 10.
    Truce, W.E., Heuring, D.L., and Wolf, G.C., J. Org. Chem., 1974, vol. 39, p. 238.CrossRefGoogle Scholar
  11. 11.
    Moskvichev, Yu.A., Sapunov, V.A., and Mironov, G.S., Zh. Prikl. Khim., 1980, vol. 53, p. 1619.Google Scholar
  12. 12.
    Organikum. Organisch-chemisches Grundpraktikum, Berlin: Wissenschaften, 1976, 15th edn. Translated under the title Organikum, Moscow: Mir, 1979, vol. 1, p. 405.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2010

Authors and Affiliations

  • A. A. Pudikova
    • 1
  • N. P. Gerasimova
    • 1
  • Yu. A. Moskvichev
    • 1
  • E. M. Alov
    • 1
  • A. S. Danilova
    • 1
  • O. S. Kozlova
    • 1
  1. 1.Yaroslavl State Technical UniversityYaroslavlRussia

Personalised recommendations