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Enantiomerically pure (R)-1-(1-phenylethyl)imidazoles 4a,b can be prepared conveniently from alfa-(hydroxyimino)ketones 1, (R)-1-phenylethylamine and form aldehyde, fol lowed by deoxygenation with Raney-Ni. Similarly, the reaction with (R,R)-trans-cyclohexane-1,2-diamine yields enantiomerically pure (R,R)-trans-1,1'-cyclohexane-1,2-diyl)imidazoles 4c,d. Alkylation of these imidazole derivatives with alkylbromides leads to the corresponding 3-alkylimidazolium bromides 6 and 8, respectively, which on treatment with sodium tetrafluoroborate are transformed into the correspond ing tetrafluoroborates 7 and 9. Whereas some of the imidazolium salts 7 show properties of chiral ionic liquids, the bis-imidazolium tetrafluoroborates 9 are high-melting crystalline materials.
Słowa kluczowe
Wydawca
Czasopismo
Rocznik
Tom
Strony
1105--1114
Opis fizyczny
Bibliogr. 22 poz., rys.
Twórcy
autor
autor
autor
autor
autor
autor
- Department of Organic and Applied Chemistry, University of Łódź, Narutowicza 68, PL-90-136 Łódź, Poland, gmloston@uni.lodz.pl
Bibliografia
- 1. a) Wasserscheid P. and Welton T., 'Ionic Liquids in Synthesis', Wiley-VCH, Weinheim, 2008;b) Dyson P.J. and Geldbach T. J., 'Metal Catalyzed Reactions in Ionic Liquids', Springer, Stuttgart, 2005;c) Ohno H. (Ed.), 'Electrochemical aspects of ionic liquids', Wiley, New York, 2005.
- 2. a) Welton T., Chem. Rev., 99, 2071 (1999); b) Dupont J., de Souza R.F. and Suarez P.A.Z., Chem. Rev., 102,3667 (2002); c) Headley A.D. and Ni B.,Aldrichim. Acta, 40,107 (2007); d) Paczal A. and Kotschy A., Monatsh. Chem., 138,1115 (2007); e) Chen X., Li X., Hu A. and Wang F., Tetrahedron: Asymmetry, 19, 1 (2008); f) Bica K. and Gaertner P., Eur. J. Org. Chem., 3235 (2008).
- 3. a) Lettau H., Nuhn P., Schneider R. and Stenger P., Pharmazie, 45, 830 (1990); b) Suwiński J., Szczepankiewicz W., Świerczek K. and Walczak K., Eur. J. Org. Chem. 1080 (2003); c) Sivek R., BureS F., Pytela O. and Kulhanek J., Molecules, 13,2326 (2008); d) Kulhanek J., BureS R, Śimin P. and Schweizer W.B., Tetrahedron: Asymmetry, 19, 2462 (2008); e) Sivek R, Pytela O. and BureS R,J. Heterocycl. Chem., 45, 1621 (2008); f) Marek A., Kulhanek J. and BureS F., Synthesis, 325 (2009).
- 4. Bao W, Wang Z. and Li X., J. Org. Chem., 68, 591 (2003).
- 5. a) Jasiński M., Mlostoń G., Linden A. and Heimgartner H., Helv. Chim. Acta, 91, 1916 (2008); b) Mlostoń G., Romański J., Jasiński M. and Heimgartner H., Tetrahedron: Asymmetry, in press.
- 6. a) Genisson Y, Lauth-de Viguerie N., Andrć C, Baltas M. and Gorrichon L., Tetrahedron: Asymmetry, 16, 1017 (2005); b) Ding J., Desikan V., Han X., Xiao T.L., Ding R., Jenks W.S. and Armstrong D.W., Org. Lett., 1, 335 (2005).
- 7. Mlostoń G., Mucha P., Urbaniak K., Broda K. and Heimgartner H., Helv. Chim. Acta, 91, 232 (2008).
- 8. a) Matsuoka Y, Ishida Y, SasokiD. and SaigoK., Tetrahedron, 62,8199 (2006); b) Jasiński M., Mlostoń G., Mucha P., Linden A. and Heimgartner H., Helv. Chim. Acta, 90, 1765 (2007).
- 9. Mucha P., Mlostoń G., Jasiński M., Linden A. and Heimgartner H., Tetrahedron: Asymmetry, 19, 1600 (2008).
- 10. Johnson C.K., ORTEPII. Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
- 11. a) Semon WL. and Damerell V.R., Org. Synth. Coll., Vol. 2,205 (1943); b) Bennett G.B., MasonR.B., AldenL.J. and Roach Jr., i.B.,J. Med. Chem.,21,623 (1978); c) Taylor T.W.J, and Marks M.S., J. Chem. Soc, 2302(1930).
- 12. Min G.H., Yim T, Lee H.Y, Huh D.H., Lee E., Mun J., Oh S.M. and Kim Y.G., Bull. Korean Chem. Soc, 27, 847 (2006).
- 13. Hooft R., KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
- 14. Otwinowski Z. and Minor W., in 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallogra-phy', Part A, Eds. Carter C.W, Jr. and Sweet R.M., Academic Press, New York, 1997, p. 307.
- 15. Blessing R.H., Acta Crystallogr., Sect. A, 51, 33 (1995).
- 16. Altomare A., Cascarano G., Giacovazzo C, Guagliardi A., Burla M.C., Polidori G. and Camalli M., SIR92, J. Appl. Crystallogr., 11, 435 (1994).
- 17. Spek A.L., PLATON, Program for the Analysis of Molecular Geometry. University of Utrecht, The Netherlands, 2008.
- 18. a) Flack H.D. and Bernardinelli G., Acta Crystallogr., Sect. A, 55, 908 (1999); b) Flack H.D. and Bernardinelli G., J. Appl. Crystallogr., 33, 1143 (2000).
- 19. a) Maslen E.N., Fox A.G. and O'Keefe M.A., in 'International Tables for Crystallography', Ed. Wilson A.J.C., Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 6.1.1.1, p. 477; b) Creagh D.C. and McAuley W.J., ibid., Table 4.2.6.8, p. 219; c) Creagh D.C. and Hubbell J.H., ibid., Table 4.2.4.3, p. 200.
- 20. Stewart R.F., Davidson E.R. and Simpson W.T., J. Chem. Phys., 42, 3175 (1965).
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- 22. Sheldrick G.M., SHELXL97, Program for the Refinement of Crystal Structures, University of Góttingen, Germany, 1997.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ5-0028-0053