Russian Journal of Organic Chemistry

, Volume 48, Issue 12, pp 1530–1535 | Cite as

Oxidative addition of trifluoromethanesulfonamide to cycloalkadienes

  • M. Yu. Moskalik
  • V. V. Astakhova
  • B. A. Shainyan


Reactions of trifluoromethanesulfonamide with cyclopentadiene, cyclohexa-1,3- and -1,4-dienes, cyclohepta-1,3,5-triene, and cycloocta-1,3-diene in the presence of t-BuOCl-NaI were studied. Trifluoromethanesulfonamide added at one double bond of cyclopentadiene and cyclohexa-1,3-diene in regio- and stereoselective fashion to give N-(5-iodocyclopent-2-en-1-yl)trifluoromethanesulfonamide and trans-N,N′-cyclohex-3-ene-1,2-diylbis(1,1,1-trifluoromethanesulfonamide), respectively. The reaction with cyclohexa-1,4-diene involved both isolated double bonds to produce N,N′-(2-chloro-5-iodocyclohexane-1,4-diyl)bis(1,1,1-trifluoromethanesulfonamide) which underwent halophilic reduction of the CHI group by the action of NaI and elimination of HCl, leading to N,N′-(cyclohex-2-ene-1,4-diyl)bis(1,1,1-trifluoromethanesulfonamide). Under analogous conditions, cyclohepta-1,3,5-triene was oxidized to benzaldehyde, while no reaction with trifluoromethanesulfonamide occurred.


Diene Cyclopentadiene Trifluoro Sodium Iodide Methanesulfonamide 
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  1. 1.
    Shainyan, B.A., Moskalik, M.Yu., Starke, I., and Schilde, U., Tetrahedron, 2010, vol. 66, p. 8383; Moskalik, M.Yu. and Shainyan, B.A., Russ. J. Org. Chem., 2011, vol. 47, p. 568; Shainyan, B.A., Moskalik, M.Yu., and Astakhova, V.V., Russ. J. Org. Chem., 2012, vol. 48, p. 918.CrossRefGoogle Scholar
  2. 2.
    Moskalik, M.Yu., Shainyan, B.A., and Schilde, U., Russ. J. Org. Chem., 2011, vol. 47, p. 1271.CrossRefGoogle Scholar
  3. 3.
    Knight, J.G. and Muldowney, M.P., Synlett, 1995, p. 949.Google Scholar
  4. 4.
    Ma, L., Du, M.-D., and Xu, J., Chirality, 2006, vol. 18, p. 575.CrossRefGoogle Scholar
  5. 5.
    Wu, Q., Hu, J., Ren, X., and Zhou, J., Chem. Eur. J., 2011, vol. 17, p. 11 553.Google Scholar
  6. 6.
    Mukhopadhay, M., Reddy, M.M., Maikap, G.C., and Iqbal, J., J. Org. Chem., 1995, vol. 60, p. 2670; Nishibayashi, Y., Chiha, T., Ohe, K., and Uemura, S., J. Chem. Soc., Chem. Commun., 1995, p. 1243; Magnus, P., Lacour, J., Coldham, I., Mugrage, B., and Bauta, W.B., Tetrahedron, 1995, vol. 51, p. 11 087; Katz, T.J. and Shi, S., J. Org. Chem., 1994, vol. 59, p. 8297.CrossRefGoogle Scholar
  7. 7.
    Sharpless, K.B., Hori, T.L., Truesdale, K., and Dietrich, C., J. Am. Chem. Soc., 1976, vol. 98, p. 269; Brunko, M., Khuong, T.-A.V., and Sharpless, K.B., Angew. Chem., Int. Ed. Engl., 1996, vol. 35, p. 454.CrossRefGoogle Scholar
  8. 8.
    Magnus, P., Lacour, J., Bauta, W., Mugrage, B., and Lynch, V., J. Chem. Soc., Chem. Commun., 1991, p. 1362; Singer, S. and Sharpless, K.B., J. Org. Chem., 1978, vol. 43, p. 1448.Google Scholar
  9. 9.
    Yeh, M.-C., Pai, H.-F., Lin, Z.-J., and Lee, B.-R., Tetrahedron, 2009, vol. 65, p. 4789.CrossRefGoogle Scholar
  10. 10.
    Backvall, J.-B. and Andersson, P.G., J. Am. Chem. Soc., 1990, vol. 112, p. 3683.CrossRefGoogle Scholar
  11. 11.
    Morita, N. and Krause, N., Org. Lett., 2004, vol. 6, p. 4121.CrossRefGoogle Scholar
  12. 12.
    Sisko, J. and Weinreb, S.M., Tetrahedron Lett., 1989, vol. 30, p. 3037.CrossRefGoogle Scholar
  13. 13.
    Ginner, X. and Najera, C., Synlett, 2009, p. 3211; Qin, H., Yamagiva, N., Matsunaga, S., and Shibasaki, M., J. Am. Chem. Soc., 2006, vol. 128, p. 1611.Google Scholar
  14. 14.
    Horiuchi, C.A., Hosokawa, H., Kanamori, M., Muramatsu, Y., Ochiai, K., and Takahashi, E., Chem. Lett., 1995, vol. 24, p. 13.CrossRefGoogle Scholar

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© Pleiades Publishing, Ltd. 2012

Authors and Affiliations

  • M. Yu. Moskalik
    • 1
  • V. V. Astakhova
    • 1
  • B. A. Shainyan
    • 1
  1. 1.Favorskii Irkutsk Institute of Chemistry, Siberian DivisionRussian Academy of SciencesIrkutskRussia

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