Advertisement

Russian Journal of Organic Chemistry

, Volume 44, Issue 2, pp 311–316 | Cite as

Oxymethylation of trifluoromethanesulfonamide with paraformaldehyde in ethyl acetate

  • V. I. Meshcheryakov
  • M. Yu. Moskalik
  • A. Kelling
  • U. Schilde
  • I. A. Ushakov
  • B. A. Shainyan
Article

Abstract

Acid-catalyzed reaction of trifluoromethanesulfonamide with paraformaldehyde in ethyl acetate led to the formation of oxymethylated products that did not form in the reaction carried out in sulfuric acid. Following products were obtained: 5-trifluoromethylsulfonyl-1,3-dioxazinane, 3,7-bis-(trifluoromethylsulfonyl)-1,5,3,7-dioxadiazocane, and a complex of trifluoromethanesulfonamide with 2,4,8,10-tetraoxospiro[5,5]undecene, 1:1. The spiroring resulted from the cyclization of pentaerythritol under the action of formaldehyde. The pentaerythritol formed in its turn by oxymethylation of the methyl group of ethyl acetate with paraformaldehyde followed by the reduction of the COOEt group into CH2 OH by the formaldehyde.

Keywords

Pentaerythritol Undecene Trifluoromethylsulfonyl Methanesulfonamide Trifluoromethanesulfonamide 
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.
    Meshcheryakov, V.I., Albanov, A.I., and Shainyan, B.A., Zh. Org. Khim., 2005, vol. 41, p. 1409.Google Scholar
  2. 2.
    Shainyan, B.A., Ushakov, I.A., Mescheryakov, V.I., Schilde, U., Koch, A., and Kleinpeter, E., Tetrahedron, 2007, vol. 63, p. 11828.CrossRefGoogle Scholar
  3. 3.
    Shainyan, B.A., Mescheryakov, V.I., Albanov, A.I., and Sigalov, M.V., Tetrahedron Lett., 2005, vol. 46, p. 6199.CrossRefGoogle Scholar
  4. 4.
    Fritschi, S. and Vasella, A., Helv. Chim. Acta, 1991, vol. 74, p. 2024.CrossRefGoogle Scholar
  5. 5.
    Hendrickson, J.B., J. Am. Chem. Soc., 1967, vol. 89, p. 7036.CrossRefGoogle Scholar
  6. 6.
    Shainyan, B.A., Ushakov, I.A., Koch, A., and Kleinpeter, E., J. Org. Chem., 2006, vol. 71, p. 7638.CrossRefGoogle Scholar
  7. 7.
    Sheldrick, G.M., SHELXS-97. Program for Crystal Structure Solution, Guttingen, 1997.Google Scholar
  8. 8.
    Sheldrick, G.M., SHELXL-97. Program, for Crystal Structure Refinement, Guttingen, 1997.Google Scholar
  9. 9.
    Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery, J.A., Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J.M., Daniels, A.D., Kudin, K.N., Strain, M.C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G.A., Ayala, P.Y., Cui, Q., Morokuma, K., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J.V., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nana-yakkara, A., Gonzalez, C., Challacombe, M., Gill, P.M.W., John-son, B., Chen, W., Wong, M.W., Andres, J. L., Gonzalez, C., Head-Gordon, M., Replogle, E.S., and Pople, J.A., Gaussian 98, Revision A.6, Gaussian, Inc., Pittsburgh, PA, 1998.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2008

Authors and Affiliations

  • V. I. Meshcheryakov
    • 1
  • M. Yu. Moskalik
    • 1
  • A. Kelling
    • 2
  • U. Schilde
    • 2
  • I. A. Ushakov
    • 1
  • B. A. Shainyan
    • 1
  1. 1.Faworsky Irkutsk Institute of Chemistry, Siberian DivisionRussian Academy of SciencesIrkutskRussia
  2. 2.Chemisches Institut der Universität PotsdamPotsdamGermany

Personalised recommendations