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

  • M. Yu. Moskalik
  • V. I. Meshcheryakov
  • B. A. Shainyan
Article

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.

Keywords

Aminomethyl Succinimide Phthalimide Trifluoromethylsulfonyl Trifluoromethane 
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.

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Copyright information

© Pleiades Publishing, Ltd. 2009

Authors and Affiliations

  • M. Yu. Moskalik
    • 1
  • V. I. Meshcheryakov
    • 1
  • B. A. Shainyan
    • 1
  1. 1.Faworsky Irkutsk Institute of Chemistry, Siberian DivisionRussian Academy of SciencesIrkutskRussia

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