Ionic liquids - deanol derivatives as the Diels-Alder reaction solvents

• Authors: Ewa Janus , Anna Syguda , Katarzyna Materna
• Languages of publication: EN

Abstracts

EN

The Diels-Alder reaction between cyclopentadiene and dienophiles in deanol derivatives containing bis(trifluoromethylsulfonyl)imide anion as media have been studied. The effect of the substituents attached to the cation on the endo:exo selectivity as well as the reaction yield have been evaluated in the absence and presence of Lewis acid catalyst - Y(OTf)3. Catalytic activity of metal triflates and the recycling of chosen catalytic systems have also been investigated [...]

Keywords

EN

Ionic liquids; Diels-Alder reaction; Lewis acids; Deanol derivatives

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2010
• Volume: 8
• Issue: 5
• Pages: 1140-1146

Dates

published

1 - 10 - 2010

online

5 - 9 - 2010

Contributors

author

Ewa Janus

• Department of Organic Chemical Technology, West Pomeranian University of Technology, 70-322, Szczecin, Poland

author

Anna Syguda

• Department of Chemical Technology, Poznan University of Technology, 60-965, Poznań, Poland

author

Katarzyna Materna

• Department of Chemical Technology, Poznan University of Technology, 60-965, Poznań, Poland

References

• [1] D.C. Rideout, R. Breslow, J. Am. Chem. Soc. 102, 7816 (1980) http://dx.doi.org/10.1021/ja00546a048[Crossref]
• [2] P.A. Grieco, K. Yoshida, P. Garner, J. Org. Chem. 48, 3137 (1983) http://dx.doi.org/10.1021/jo00166a051[Crossref]
• [3] R. Breslo, U. Maitra, Tetrahedron Lett. 25 1239 (1984) http://dx.doi.org/10.1016/S0040-4039(01)80122-2[Crossref]
• [4] U. Pindur, G. Luft, C. Otto, Chem. Rev. 93, 741 (1993) http://dx.doi.org/10.1021/cr00018a006[Crossref]
• [5] A. Kumar, Chem. Rev. 101, 1 (2001) http://dx.doi.org/10.1021/cr990410+[Crossref]
• [6] M.J. Earle, P. B. McCormac, K.R. Seddon, Green. Chem. 1, 23 (1999) http://dx.doi.org/10.1039/a808052f[Crossref]
• [7] D. Sarma, A. Kumar, Applied Catal. A. General 335, 1 (2008) http://dx.doi.org/10.1016/j.apcata.2007.10.026[Crossref]
• [8] I. Lopez, G. Silvero, M.J. Arevalo, R. Babiano, J.C. Palacios, J.L. Bravo, Tetrahedron 63, 2901 (2007) http://dx.doi.org/10.1016/j.tet.2007.01.031[Crossref]
• [9] G. Silvero, M.J. Arevalo, J. L. Bravo, M. Avalos, J. L. Jimenez, I. Lopez, Tetrahedron 61, 7105 (2005) http://dx.doi.org/10.1016/j.tet.2005.05.064[Crossref]
• [10] F. Fu, Y.Ch. Teo, T.P. Loh, Org. Lett. 8, 5999 (2006) http://dx.doi.org/10.1021/ol062481i[Crossref]
• [11] J.S. Yadav, B.V.S. Reddy, G. Kondaji, S. Sowjanya, K. Nagaiah, J. Mol. Catal. A: Chem. 258, 361 (2006) http://dx.doi.org/10.1016/j.molcata.2006.07.016[Crossref]
• [12] A. Dramska, M. Antoszczyszyn, E. Janus, Przem. Chem. 85/1, 47 (2006)
• [13] K. Takahashi, H. Nakano, R. Fujita, Chem. Comm. 3, 263 (2007) http://dx.doi.org/10.1039/b611228e[Crossref]
• [14] S. Doherty, P. Goodrich, C. Hardacre, J.G. Knight, M.T.V. Nguyen, I.Ch.P. Parvulescu, Adv. Synth. Catal. 347, 951 (2007) http://dx.doi.org/10.1002/adsc.200600531[Crossref]
• [15] N.A. Mirgane, S.B. Kotwal, A.V. Karnik, Cent. Eur. J. Chem. 8, 356 (2010) http://dx.doi.org/10.2478/s11532-009-0136-6[Crossref]
• [16] D. Yin, Ch. Li, B. Li, L. Tao, D. Yin, Adv. Synth. Catal. 347, 137 (2005) http://dx.doi.org/10.1002/adsc.200404154[Crossref]
• [17] E. Janus, I. Goc-Maciejewska, M. Łożyński, J. Pernak, Tetrahedron Lett. 47, 4079 (2006) http://dx.doi.org/10.1016/j.tetlet.2006.03.172[Crossref]
• [18] K. Nobuoka, S. Kitaoka, K. Kunimitsu, M. Lio, T. Harran, A. Wakisaka, Y. Ishikawa, J. Org. Chem. 70, 10106 (2005) http://dx.doi.org/10.1021/jo051669x[Crossref]
• [19] R.M.A. Pinto, J.A.R. Salvador, C. Le Roux, Catal. Commun. 9, 465 (2008) http://dx.doi.org/10.1016/j.catcom.2007.07.022[Crossref]
• [20] O. Bortolini, A. De Nino, A. Garofalo, L. Maiuolo, A. Procopio, B. Russo, Appl. Catal. A. General 372, 124 (2010) http://dx.doi.org/10.1016/j.apcata.2009.10.020[Crossref]
• [21] P. Ludley, N. Karodia, Tetrahedron Lett. 42, 2011 (2001) http://dx.doi.org/10.1016/S0040-4039(01)00064-8[Crossref]
• [22] P. Ludley, N. Karodia, ARKIVOC 172 (2002)
• [23] E. Janus, W. Stefaniak, Catal. Lett. 105 (2008)
• [24] A.P. Abbott, G. Capper, D.L. Davies, H.L. Munro, R.K. Rasheed, V. Tambyrajah, Chem. Comm. 19, 2010 (2001) http://dx.doi.org/10.1039/b106357j[Crossref]
• [25] A.P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed, V. Tambyrajah, Green Chem. 4, 24 (2002) http://dx.doi.org/10.1039/b108431c[Crossref]
• [26] A.P. Abbott, G. Capper, S. Gray, Chem. Phys. Chem. 7, 803 (2006)
• [27] J. Pernak, P. Chwała, A. Syguda, Polish J. Chem. 78 539 (2004)
• [28] J. Pernak, A. Syguda, I. Mirska, A. Pernak, J. Nawrot, A. Prądzyńska, S.T. Griffin, R.D. Rogers, Chem. Eur. J. 13(24), 6817 (2007) http://dx.doi.org/10.1002/chem.200700285[Crossref]
• [29] A. Vidiš, C.A. Ohlin, G. Laurenczy, E. Küsters, G. Sedelmeier, P.J. Dyson, Adv. Synth. Catal. 347, 266 (2005) http://dx.doi.org/10.1002/adsc.200404301[Crossref]
• [30] J.L. Bravo, I. Lopez, P. Cintas, G. Silvero, M.J. Arevalo, Ultrasonic Sonochemistry 13, 408 (2006) http://dx.doi.org/10.1016/j.ultsonch.2005.07.001[Crossref]

Identifiers

DOI

10.2478/s11532-010-0092-1