Tunable aryl alkyl ionic liquids (TAAILs): The next generation of ionic liquids

Angewandte Chemie - International Edition

Volumn 48, Issue 42, 2009, Pages 7908-7910

  Ahrens, Sebastian ^b   Peritz, Anke ^a   Strassner, Thomas ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b BASF SE   (Germany)

Author keywords

Imidazolium salts; Ionic liquids; Substituent effects; TAAILs

Indexed keywords

ALIPHATIC SUBSTITUENTS; ELECTRONIC INTERACTIONS; IMIDAZOLIUM; IMIDAZOLIUM RING; IMIDAZOLIUM SALTS; IMIDAZOLIUM-BASED IONIC LIQUID; METHYL DERIVATIVES; SUBSTITUENT EFFECTS; TAAILS;

ALKYLATION; AROMATIC COMPOUNDS; IONIZATION OF LIQUIDS; IONS; SALTS;

IONIC LIQUIDS;

EID: 70349682459     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200903399     Document Type: Article

References (16)

1. Ionic Liquids in Synthesis (Eds.: P. Wasserscheid, T. Welton) 2008, Wiley-VCH, Weinheim.
2. N. V. Plechkova, K. R. Seddon, Chem Soc. Rev. 2008, 37, 123.
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4. X H. Davis, Jr., P. Wasserscheid in Ionic Liquids in Synthesis (Eds.: P. Wasserscheid, T. Welton), 2008, Wiley-VCH, Weinheim, p. 45.
5. P. H. J. Kouwer, T. M. Swager, J. Am. Chem. Soc. 2007, 129, 14042.
6. S. Ahrens, T. Strassner, WO2009/095012, 2009.
7. M. A. Taige, A. Zeller, S. Ahrens, S. Goutal, E. Herdtweck, T. Strassner, J. Organomet. Chem. 2007, 692,1519.
8. T. Strassner, Top. Organomet, Chem. 2007, 22,125.
9. T. Strassner, S. Ahrens, unpublished results.
10. 4, and the solvent is removed in vacuo. The product is subsequently purified by distillation or recrystallization.
11. A tube is filled with l-N-substituted imidazole (l.0equiv) dissolved in THF (10mL) and haloalkane (1.1 equiv) and then sealed. The reaction mixture is heated to 80-110 °C in the sealed tube for 8-10 h. Filtration furnishes the solid precipitate, which is washed several times with THF and dried in vacuo.
12. T. Eicher, S. Hauptmann, H. Suschitzky, The Chemistry of Heterocycles, Wiley-VCH, Weinheim, 2003.
13. 4 and filtered, and the solvent is removed in vacuo.
14. 4 and filtered, and the solvent is removed in vacuo.
15. D. Meyer, T. Strassner, unpublished results.
16. All calculations were performed with Gaussian 03 using the density functional/Hartree-Fock hybrid model Becke3LYP and the split valence triple-Ç (TZ) basis set 6-311 + + G(d,p). No symmetry or internal coordinate constraints were applied during optimizations. Details and references are given in the Supporting Information