Mg(OTf)2 + ionic liquid - recyclable catalytic system in diels-alder reaction

• Authors: Bożena Bittner , Eugeniusz Milchert , Ewa Janus
• Languages of publication: EN

Abstracts

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.

Keywords

EN

Diels-Alder reaction; ionic liquids; Lewis acids; norbornene derivatives

• Publisher: De Gruyter Open
• Journal: Polish Journal of Chemical Technology
• Year: 2010
• Volume: 12
• Issue: 3
• Pages: 3-5

Dates

published

1 - 1 - 2010

online

27 - 9 - 2010

Contributors

author

Bożena Bittner

• Institute of Organic Chemical Technology, West Pomeranian University of Technology, ul. Pułaskiego 10, 71-322 Szczecin, Poland

author

Eugeniusz Milchert

• Institute of Organic Chemical Technology, West Pomeranian University of Technology, ul. Pułaskiego 10, 71-322 Szczecin, Poland

author

Ewa Janus

• Institute of Organic Chemical Technology, West Pomeranian University of Technology, ul. Pułaskiego 10, 71-322 Szczecin, Poland

References

• Tarasow, T. M. & Eaton, B. E. (1999) The Diels-Alder reaction and biopolymer catalysis, Cellular and Molecular Life Sciences, 55, 1463-1472. doi: 1420-682X:99:111463-10.
• Ilker M. F. & Schuke H., Coughlin E. B. Modular norbornene derivatives for the preparation of well-defined amphiphilic polymers: Study of the lipid membrane disruption activities. Macromolecules, 37(3), 694-700. doi: 10.1021/ma035407d.[Crossref]
• Willson, C. G., Okoroanyanwu, U. & Medieros, D. (2000). US Patent No. 6103445-Photoresist compositions comprising norbornene derivative polymers with acid labile groups.
• Diels O. & Alder K. (1931) Synthesen in der hydroaromatischen Reihe; XII. Mitteilung. "Dien-Synthesen" sauerstoffhaltiger Heteroringe.2. Dien-Synthesen des Furans. Ann. Chem. 490, 243-257.
• Pocker Y. & Ellsworth, D. L., (1977). Electrostatic Catalysis by Ionic Aggregates. 4. Rearrangement of 1 -Phenylallyl Chloride in Lithium Perchlorate Solutions in Aprotic Solvents. J. Am. Chem. Soc. 99, 2276-2284. doi: 10.1021/ja00449a042.
• Weinstein, R. D., Renslo, A. R., Danheiser, R. L., Harris, J. G. & Tester, J. W. (1996). Kinetic Correlation of Diels-Alder Reactions in Supercritical Carbon Dioxide. J. Phys. Chem. 100, 12337-12341. doi: 10.1021/jp960180.[Crossref]
• Fringuelli, F. & Tachici, A. (2002). Wiley. The Diels-Alder reaction: selected practical methods. (pp. 251-278).
• Silvero, G., Arevalo, M. J., Bravo, J. L., Avalos, M., Jimenez, J. L. & Lopez, I. (2005) An in-depth look at the effect of Lewis acid catalysts on Diels-Alder cycloadditions in ionic liquids. Tetrahedron, 61, 7105-7111. doi:10.1016/j.tet.2005.05.064[Crossref]
• Kobayashi, S., Hachiya, I., Araki, M. & Ishitani, H., (1993) 4,4'-di-tert-butylbiphenyl-catalysed lithiation of 2,3-dichloropropene: A Barbier-type practical alternative to 2,3-dilithiopropene. Tetrahedron Letters, 34, 1755-3758. doi:10.1016/S0040-4039(00)91989-0.[Crossref]
• Otto, G., Boccaletti, J. B. & Engberts, F. N., (1998) A Chiral Lewis-Acid-Catalyzed Diels-Alder Reaction. Water-Enhanced Enantioselectivity. J. Am. Chem. Soc. 120, 4238-4239. doi: 10.1021/ja972772+.[Crossref]
• Kumar, A. & Pawar, S. S. (2004) Converting exo-Selective Diels-Alder Reaction to endo-Selective in Chloroloaluminate Ionic Liquids. J. Org. Chem. 69, 1419-1420. doi: 10.1021/jo035038j.[Crossref]
• Yin, D., Li, C., Li, B., Tao, L. & Yin, D., (2005) High Regioselective Diels-Alder Reaction of Myrcene with Acrolein Catalyzed by Zinc-Containing Ionic Liquids. Adv. Synth. Catal. 347, 137-142. doi: 10.1002/adsc.200404233.[Crossref]
• Lopez, I., Silvero, G., Arevalo, M. J., Babiano, R., Palacios, J. C. & Bravo, J. L. (2007). Enhanced Diels-Alder reactions: on the role of mineral catalysts and microwave irradiation in ionic liquids as recyclable media. Tetrahedron, 63, 2901-2906. doi:10.1016/j.tet.2007.01.031.[Crossref]
• Sarma, D. & Kumar, A., (2008) Rare earth metal triflates promoted Diels-Alder reactions in ionic liquids. Appl. Catal. A: Gen. 335, 1-6. doi:10.1016/j.apcata.2007.10.026.[WoS][Crossref]
• Bortolini, O. D., Nino, A., Garofalo, A., Maiuolo, L., Procopio, A. & Russo B. (2010) Erbium triflate in ionic liquids: A recyclable system of improving selectivity in Diels-Alder reactions. Appl. Catalysis A: General, 372, 124-129. doi:10.1016/j.apcata.2009.10.020.[Crossref][WoS]
• Song, Ch. E., Shim, W. H., Roh, E. J., Lee, S., Choi, J. H., (2001) Ionic liquids as powerful media in scandium triflate catalysed Diels-Alder reactions: significant rate acceleration, selectivity improvement and easy recycling of catalyst Chem. Commun., 1122-1123. doi: 10.1039/b101140p.[Crossref]
• Vidis, A., Kusters, E., Sedelmeier, G. & Dyson, P. J., (2008) Effect of Lewis acids on the Diels-Alder reaction in ionic liquids with different activation modes. J. Phys. Org. Chem. 21, 264-270. doi:10.1016/j.apcata.2009.10.020.[Crossref]
• Ludley, P. & Karodia, N. (2001) Phosphonium tosylates as solvents for the Diels-Alder reaction. Tetrahedron Lett., 42, 2011-2014. doi:10.1016/S0040-4039(01)00064-8[Crossref]
• Janus, E. & Bittner, B. (2010) Triethylsulfonium Bistriflimide as the Reaction Medium in Catalyzed and Uncatalyzed Cycloaddition [4 + 2]. Catalysis Lett. 134, (1-2), 147-154 doi:10.1007/s10562-009-0211-9.[Crossref][WoS]

Identifiers

DOI

10.2478/v10026-010-0023-0