Skip to main content
SpringerLink
Log in

Unexpected regio- and stereoselective reaction of 2-bromomethyl-1,3-thiaselenole with ketones. Formation of 1-[(Z)-2-(vinylsulfanyl)ethenyl]selanylalkan-2-ones

  • Short Communications
  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. Gerzson, M.F.B., Victoria, F.N., Radatz, C.S., Gomes, M.G., Boeira, S.P., and Jacob, R.G., Pharmacol., Biochem. Behav., 2012, vol. 102, p. 21.

    Article  CAS  Google Scholar 

  2. Cotgreave, I.A., Moldeus, P., Brattsand, R., Hallberg, A., Andersson, C.M., and Engman, L., Biochem. Pharmacol., 1992, vol. 43, p. 793.

    Article  CAS  Google Scholar 

  3. Engman, L., Anderson, C., Morgenstern, R., Cotgreave, I.A., Andersson, C.M., and Hallberg, A., Tetrahedron, 1994, vol. 50, p. 2929.

    Article  CAS  Google Scholar 

  4. Victoria, F.N., Radatz, C.S., Sachini, M., Jacob, R.G., Perin, G., Silva, W.P., and Eder, J.L., Tetrahedron Lett., 2009, vol. 50, p. 6761.

    Article  CAS  Google Scholar 

  5. Srivastava, P. and Engman, L., Tetrahedron Lett., 2010, vol. 51, p. 1149.

    Article  CAS  Google Scholar 

  6. Bodtke, A., Kandt, M., Pfeiffer, W.-D., and Langer, P., Phosphorus, Sulfur Silicon Relat. Elem., 2007, vol. 182, p. 209.

    Article  CAS  Google Scholar 

  7. Gramza, J., Mitchell, R.B., and Dittmer, D.C., J. Org. Chem., 1984, vol. 49, p. 2057.

    Article  CAS  Google Scholar 

  8. Otero, M.D., Batanero, B., and Barba, F., Tetrahedron, 2004, vol. 60, p. 4609.

    Article  CAS  Google Scholar 

  9. Boiko, Yu.A., Kupin, B.S., and Petrov, A.A., Zh. Org. Khim., 1969, vol. 5, p. 1553.

    CAS  Google Scholar 

  10. Bao, W. and Zhang, Y., Synlett, 1996, no. 12, p. 1187.

    Google Scholar 

  11. Huang, X. and Xu, X.-H., Synth. Commun., 1998, vol. 28, p. 807.

    Article  CAS  Google Scholar 

  12. Balasubramaniam, S. and Aidhen, I.S., Synlett, 2011, no. 11, p. 1533.

    Google Scholar 

  13. Reich, H.J. and Cohen, M.L., J. Am. Chem. Soc., 1979, vol. 101, p. 1307.

    Article  CAS  Google Scholar 

  14. Meinke, P.T. and Krafft, G.A., J. Am. Chem. Soc., 1988, vol. 110, p. 8671.

    Article  CAS  Google Scholar 

  15. George, T.G., Eur. J. Org. Chem., 2002, vol. 14, p. 2363.

    Google Scholar 

  16. Nishiyama, Y., Koguma, Y., Tanaka, T., and Umeda, R., Molecules, 2009, vol. 14, p. 3367.

    Article  CAS  Google Scholar 

  17. Sykes, P., A Guidebook to Mechanism in Organic Chemistry, Harlow, Essex, England: Longman, 1986, 6th ed. Translated under the title Mekhanizmy reaktsii v organicheskoi khimii, Moscow: Khimiya, 1991, p. 334.

    Google Scholar 

  18. Trofimov, B.A. and Amosova, S.V., Sulfur Rep., 1984, vol. 3, p. 323.

    Article  CAS  Google Scholar 

  19. Trofimov, B.A. and Amosova, S.V., Divinilsul’fid i ego proizvodnye (Divinyl Sulfide and Its Derivatives), Novosibirsk: Nauka, 1983.

    Google Scholar 

  20. Amosova, S.V., Penzik, M.V., Albanov, A.I., and Potapov, V.A., Tetrahedron Lett., 2009, vol. 50, p. 306.

    Article  CAS  Google Scholar 

  21. Amosova, S.V., Penzik, M.V., Albanov, A.I., and Potapov, V.A., Russ. J. Gen. Chem., 2009, vol. 79, p. 161.

    Article  CAS  Google Scholar 

  22. Rusakov, Y.Y., Krivdin, L.B., Potapov, V.A., Penzik, M.V., and Amosova, S.V., Magn. Reson. Chem., 2011, vol. 49, p. 389.

    Article  CAS  Google Scholar 

  23. Kalabin, G.A. and Kushnarev, D.F., Zh. Strukt. Khim., 1980, vol. 20, p. 617.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    M. V. Penzik, S. V. Amosova, A. I. Albanov & V. A. Potapov

Authors
  1. M. V. Penzik
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. V. Amosova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. I. Albanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. A. Potapov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. V. Amosova.

Additional information

Dedicated to Full Member of the Russian Academy of Sciences O.N. Chupakhin on his 80th anniversary

Original Russian Text © M.V. Penzik, S.V. Amosova, A.I. Albanov, V.A. Potapov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 6, pp. 930–932.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Penzik, M.V., Amosova, S.V., Albanov, A.I. et al. Unexpected regio- and stereoselective reaction of 2-bromomethyl-1,3-thiaselenole with ketones. Formation of 1-[(Z)-2-(vinylsulfanyl)ethenyl]selanylalkan-2-ones. Russ J Org Chem 50, 916–918 (2014). https://doi.org/10.1134/S1070428014060311

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428014060311

Keywords

Search

Navigation