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

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


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.


Aminomethyl Succinimide Phthalimide Trifluoromethylsulfonyl Trifluoromethane 
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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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