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2007 | 5 | 1 | 156-168
Article title

Alkylation of ambident indole anion in ionic liquids

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EN
Abstracts
EN
Alkylation of indole salts in different ionic liquids is reported. Ionic liquids increase the alkylation reaction rate of ambident indole anion and reduce the effects of counter ions and/or additives, the alkylation reaction rates being independent of the presence of small amounts of protic solvents or water. [...]
Publisher

Journal
Year
Volume
5
Issue
1
Pages
156-168
Physical description
Dates
published
1 - 3 - 2007
online
1 - 3 - 2007
Contributors
  • Faculty of Chemistry, University of Latvia, Riga, LV-1586, Latvia
  • Faculty of Chemistry, University of Latvia, Riga, LV-1586, Latvia
author
  • Faculty of Chemistry, University of Latvia, Riga, LV-1586, Latvia
author
  • Faculty of Chemistry, University of Latvia, Riga, LV-1586, Latvia
References
  • [1] S.T. Handy: “Room Temperature Ionic Liquids: Classes and Physical Properties”, Curr. Org. Chem., Vol. 9, (2005), pp. 959–988. http://dx.doi.org/10.2174/1385272054368411[Crossref]
  • [2] N. Jain, A. Kumar, S. Chauhan and S.M.S. Chauhan: “Chemical and biochemical transformations in ionic liquids”, Tetrahedron, Vol. 61, (2005), pp. 1015–1060. http://dx.doi.org/10.1016/j.tet.2004.10.070[Crossref]
  • [3] Z.-B. Zhou, H. Matsumoto and K. Tatsumi: “Low-melting, low-viscous, hydrophobic ionic liquids: aliphatic quaternary ammonium salts with perfluoroalkyltrifluoroborates”, Chem. Eur. J., Vol. 11, (2005), pp. 752–766. http://dx.doi.org/10.1002/chem.200400817[Crossref]
  • [4] G.W. Meindersma, A.J.G. Podt and A.B. de Haan: “Selection of ionic liquids for the extraction of aromatic hydrocarbons from aromatic/aliphatic mixtures”, Fuel Proces. Technol., Vol. 87, (2005), pp. 59–70. http://dx.doi.org/10.1016/j.fuproc.2005.06.002[Crossref]
  • [5] C. Baudequin, D. Bregeon, J. Levillain, F. Guillen, J.-C. Plaquevent and A.-C. Gaumont: “Chiral ionic liquids, a renewal for chemistry of chiral solvents? Design, synthesis and applications for chiral recognition and asymmetric synthesis”, Tetrahedron: Asymmetry, Vol. 16, (2005), pp. 3921–3945. http://dx.doi.org/10.1016/j.tetasy.2005.10.026[Crossref]
  • [6] K.N. Marsh, J.A. Boxall, R. Lichtenthaler: “Room temperature ionic liquids and their mixtures - a review”, Fluid Phase Equilibr., Vol. 219, (2004), pp. 93–98. http://dx.doi.org/10.1016/j.fluid.2004.02.003[Crossref]
  • [7] C.F. Poole: “Chromatographic and spectroscopic methods for the determination of solvent properties of room temperature ionic liquids”, J. Chromatogr. A, Vol. 1037, (2004), pp. 49–82. http://dx.doi.org/10.1016/j.chroma.2003.10.127[Crossref]
  • [8] P. Kubisa: “Application of ionic liquids as solvents for polimerization processes”, Progr. Polym. Sci., Vol. 29, (2004), pp. 3–12. http://dx.doi.org/10.1016/j.progpolymsci.2003.10.002[Crossref]
  • [9] P. Wasserscheid and T. Welton: Ionic Liquids in Synthesis, VCH, Weinheim, 2003.
  • [10] M.A. Abraham and L. Moens: Clean Solvents: Alternative Media for Chemical Reactions and Processing, ACS Symposium Series 819, ACS, Washington DC, 2002.
  • [11] R. Sheldon: “Catalytic reactions in ionic liquids”, Chem. Commun., (2001), pp. 2399–2407. [Crossref]
  • [12] P. Wasserscheid and W. Keim: “Ionic liquids - new „solutions“ for transition metal catalysis”, Angew. Chem., Int. ed., Vol. 39, (2000), pp. 3772–3789. http://dx.doi.org/10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5[Crossref]
  • [13] R.D. Rogers and K.R. Seddon: Ionic Liquids: Industrial Application to Green Chemistry, ACS Symposium Series 818, ACS, Washington DC, 2002.
  • [14] T. Welton: “Room-temperature ionic liquids. Solvents for synthesis and catalysis”, Chem. Rev., Vol. 99, (1999), pp. 2071–2083. http://dx.doi.org/10.1021/cr980032t[Crossref]
  • [15] G. Shao: “C-alkylation of 1,3-dicarbonyl compounds in ionic liquids”, Hecheng Huaxue, Vol. 11, (2003), pp. 6–8; Chem. Abstr., Vol. 139, (2003), art. 116960f.
  • [16] G.V. Kryshtal, G.M. Zhdankina and S.G. Zlotin: “Alkylation of malonic and acetoacetic esters in an ionic liquid”, Mendeleev Commun., (2002), pp. 57–59. [Crossref]
  • [17] M.J. Earle, P.B. McCormac and K.R. Seddon: “The first high yield green route to a pharmaceutical in a room temperature ionic liquid”, Green Chem., Vol. 2, (2000), pp. 261–262. http://dx.doi.org/10.1039/b006612p[Crossref]
  • [18] M.J. Earle, P.B. McCormac and K.R. Seddon: “Regioselective alkylation in ionic liquids”, Chem. Commun., (1998), pp. 2245–2246. [Crossref]
  • [19] J. March: Advanced Organic Chemistry, 3rd ed., John Wiley and Sons, New York, 1985.
  • [20] M.G. Reinecke, J.F. Sebastian, H.W. Johnson and C. Pyun: “The effect of solvent and cation on the reaction of organometallic derivatives of indole with methyl iodide”, J. Org. Chem., Vol. 37, (1972), pp. 3066–3068. http://dx.doi.org/10.1021/jo00985a005[Crossref]
  • [21] B. Cardillo, G. Casnati, A. Pochini and A. Ricca: “Alkylation of indole sodium salt as ambifunctional nucleophilic system”, Tetrahedron, Vol. 23, (1967), pp. 3771–3783. http://dx.doi.org/10.1016/0040-4020(67)80025-5[Crossref]
  • [22] Y.G. Jorapur, J.M. Jeong and D.Y. Chi: “Potassium carbonate as a base for the N-alkylation of indole and pyrrole in ionic liquids”, Tetrahedron Lett., Vol. 47, (2006), pp. 2435–2438. http://dx.doi.org/10.1016/j.tetlet.2006.01.129[Crossref]
  • [23] J.G. Huddleston, H.D. Willauer, R.P. Swatloski, A.E. Visser and R.D. Rogers: “Room temperature ionic liquids as novel media for ‘clean’ liquid-liquid extraction”, Chem. Commun., (1998), pp. 1765–1766. [Crossref]
  • [24] T. Nishida, Y. Tashiro and M. Yamamoto: “Physical and electrochemical properties of 1-alkyl-3-methylimidazolium tetrafluoroborate for electrolyte”, J. Fluorine Chem., Vol. 120, (2003), pp. 135–141. http://dx.doi.org/10.1016/S0022-1139(02)00322-6
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-006-0063-8
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