N-hexylpyridinium bis(trifluoromethylsulfonyl)imide and Lewis acids — catalytic systems for Diels-Alder reaction

Bożena Bittner 1 , Ewa Janus 1 , and Eugeniusz Milchert 1
  • 1 Institute of Organic Chemical Technology, West Pomeranian University of Technology, Szczecin, 70-310, Szczecin, Poland

Abstract

A comparative study of the Diels-Alder reactions between cyclopentadiene (1) and dienophiles (2 a–c) in N-hexylpyridinium bis(trifluoromethylsulfonyl)imide in a temperature range of 20–45°C is reported. The reaction rate constants and activation energies were calculated. Moreover, the catalytic systems based on N-hexylpyridinium bis(trifluoromethylsulfonyl)imide and Lewis acids were tested as a reaction media to perform the Diels-Alder reaction. Yb, Y, Mg, Zn triflates and chlorides (0.005 to 0.1 mmol) were used as catalysts. The recycling of catalytic system consisted of YCl3 and ionic liquid was performed.

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