Russian Journal of Organic Chemistry

, Volume 41, Issue 9, pp 1381–1386 | Cite as

Cascade Transformations of Trifluoromethanesulfonamide in Reaction with Formaldehyde

  • V. I. Meshcheryakov
  • A. I. Albanov
  • B. A. Shainyan


Trifluoromethanesulfonamide reacts with paraformaldehyde in acid medium to give both open-chain and cyclic condensation products: bis(trifluoromethylsulfonylamino)methane, N, N-bis(trifluoromethylsulfonylaminomethyl)trifluoromethanesulfonamide, 5-(trifluoromethylsulfonyl)dihydro-1,3,5-dioxazine, 3,5-bis(trifluoromethylsulfonyl)tetrahydro-1,3,5-oxadiazine, 1,3,5-tris(trifluoromethylsulfonyl)hexahydro-1,3,5-triazine, 5,7-bis(trifluoromethylsulfonyl)-1,3,5,7-dioxadiazocane, and 5,7,9-tris(trifluoromethylsulfonyl)-1,3,5,7,9-dioxatriazecane. Amidoalkylation of acetonitrile in the system trifluoromethanesulfonamide-paraformaldehyde-phosphoric acid leads to formation of N-(trifluoromethylsulfonylaminomethyl)acetamide.


Formaldehyde Organic Chemistry Acetonitrile Paraformaldehyde Acid Medium 
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  1. 1.
    Smolin, E.M. and Rappoport, L., The Chemistry of Heterocyclic Compounds: s-Triazines and Derivatives, Weissberger, A., Ed., New York: Interscience, 1959, p. 490.Google Scholar
  2. 2.
    Zaugg, H.E. and Martin, W.B., Organic Reactions, New York: Wiley, 1965, vol. 14.Google Scholar
  3. 3.
    Luknitskii, F.I., Chem. Rev., 1975, vol. 75, p. 259.CrossRefGoogle Scholar
  4. 4.
    Shainyan, B.A. and Meshcheryakov, V.I., Russ. J. Org. Chem., 2001, vol. 37, p. 1797.Google Scholar
  5. 5.
    Meshcheryakov, V.I., Shainyan, B.A., Tolstikova, L.L., and Albanov, A.I., Russ. J. Org. Chem., 2003, vol. 39, p. 1517.CrossRefGoogle Scholar
  6. 6.
    Meshcheryakov, V.I. and Shainyan, B.A., Russ. J. Org. Chem., 2004, vol. 40, p. 390.CrossRefGoogle Scholar
  7. 7.
    Orazi, O.O. and Corral, R.A., J. Chem. Soc., Perkin Trans. 1, 1975, p. 772.Google Scholar
  8. 8.
    Ishchenko, M.A., Nikolaev, V.D., and Sokolov, A.A., Russ. J. Org. Chem., 1996, vol. 32, p. 460.Google Scholar

Copyright information

© MAIK "Nauka/Interperiodica" 2005

Authors and Affiliations

  • V. I. Meshcheryakov
    • 1
  • A. I. Albanov
    • 1
  • B. A. Shainyan
    • 1
  1. 1.Favorskii Irkutsk Institute of Chemistry, Siberian DivisionRussian Academy of SciencesIrkutskRussia

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