Skip to main content
SpringerLink
Log in

Reaction of γ-dicarboxylic acids amides and imides with trifluoromethanesulfonamide and formaldehyde

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

Abstract

Three-component condensation of trifluoromethanesulfonamide with paraformaldehyde and succinamide depending on the reaction conditions led alongside bis(trifluoromethanesulfonamido)methane to the formation of a substitution product, bis[(trifluoromethylsulfonyl)aminomethyl]succinamide, or to a cyclization product, N-[trifluoromethylsulfonyl)aminomethyl]succinimide. The attempt to obtain the latter by the reaction of the trifluoromethanesulfonamide sodium salt CF3SO2NHNa with N-chloromethylsuccinimide unexpectedly resulted in N,N-bis(succinimidomethyl)-trifluoromethanesulfonamide. Analogously the reaction of CF3SO2NHNa with N-chloromethyl-phthalimide gave N,N-bis(phthalimidomethyl)trifluoromethanesulfonamide. The reaction of CF3SO2NHNa with succinimide and phthalimide in water and alcohol solution resulted in the ring opening and further transformation of the formed monosubstituted N-(trifluoromethylsulfonyl)amides of succinic and phthalic acids.

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

Similar content being viewed by others

References

  1. Meshcheryakov, V.I., Albanov, A.I., and Shainyan, B.A., Zh. Org.Khim., 2005, vol. 41, p. 1409.

    Google Scholar 

  2. Meshcheryakov, V.I., Moskalik, M.Yu., Kelling, A., Schilde, U., Ushakov, I.A., and Shainyan, B.A., Zh. Org.Khim., 2008, vol. 44, p. 313.

    Google Scholar 

  3. Meshcheryakov, V.I., Danilevich, Yu.S., Moskalik, M.Yu., Stetsyura, N.Yu., Zavodnik, V.E., Bel’skii, V.K., and Shainyan, B.A., Zh. Org.Khim., 2007, vol. 43, p. 799.

    Google Scholar 

  4. Bagno, A., Bujnicki, B., Bertrand, S., Comuzzi, C., Dorigo, F., Janvier, P., and Scorrano, G., Chem. Eur. J., 1999, vol. 5, p. 523.

    Article  CAS  Google Scholar 

  5. Tablitsy konstant skorosti i ravnovesiya geteroliticheskikh organicheskikh reaktsii (Tables of Rate and Equilibrium Constants of Heterocyclic Organic Reactions), Pal’m, V.A., Ed., Moscow: VINITI, 1975.

    Google Scholar 

  6. Meshcheryakov, V.I., Shainyan, B.A., Tolstikova, L.L., and Albanov, A.I., Zh. Org.Khim., 2003, vol. 39, p. 1583.

    Google Scholar 

  7. Cherbuliez, E. and Sulzer, G., Helv. Chim. Acta, 1925, vol. 8, p. 567.

    Article  CAS  Google Scholar 

  8. Zaugg, G. and Martin, V., Organicheskie reaktsii (Organic Reactions), 1967, vol. 14, p. 65.

    Google Scholar 

  9. Bohme, H., Broese, R., and Eiden, F., Chem. Ber., 1959, vol. 92, p. 1258.

    Article  CAS  Google Scholar 

  10. Jeffery, G.H. and Vogel, A.I., J. Chem. Soc., 1934, p. 1101.

Download references

Author information

Authors and Affiliations

  1. Faworsky Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, 664033, Russia

    M. Yu. Moskalik, V. I. Meshcheryakov & B. A. Shainyan

Authors
  1. M. Yu. Moskalik
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. I. Meshcheryakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. A. Shainyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. Yu. Moskalik.

Additional information

Original Russian Text © M.Yu. Moskalik, V.I. Meshcheryakov, B.A. Shainyan, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 11, pp. 1654–1659.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Moskalik, M.Y., Meshcheryakov, V.I. & Shainyan, B.A. Reaction of γ-dicarboxylic acids amides and imides with trifluoromethanesulfonamide and formaldehyde. Russ J Org Chem 45, 1644–1650 (2009). https://doi.org/10.1134/S1070428009110116

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428009110116

Keywords

Search

Navigation