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

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Bittner B., Janus E., Milchert E.
Open Chemistry
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2011
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vol. 9
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issue 1
192-198
EN
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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Mg(OTf)2+ ionic liquid - recyclable catalytic system in diels-alder reaction

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Bittner B., Milchert E., Janus E.
|
EN
A comparative study of Diels-Alder reaction between cyclopentadiene and dimethyl maleate in catalytic system is reported. The catalytic system was formed from ionic liquid which was made of N-hexylpyridinium bis(trifluoromethylsulfonyl)imide and magnesium trifluoromethanesulfonate. The yields, TONs, TOFs and endo:exo ratios were calculated. The optimal catalyst concentration was found in order to obtain the mixture of endo, exo isomers with the highest yields. Moreover recycling of the catalytic system consisting of Mg(OTf)2 (2 mol%) and ionic liquid was performed. The distillation was noticed to be a better product removal method than extraction by organic solvent, taking into consideration both the TON and TOF values.
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