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Synthesis 2003(1): 0024-0026
DOI: 10.1055/s-2003-36254
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

New Quaternary Polyfluoroalkyl-1,2,4-Triazolium Salts Leading to Ionic Liquids

Yousef R. Mirzaei, Jean’ne M. Shreeve*
Department of Chemistry, University of Idaho, Moscow, Idaho 83844-2343, USA
Fax: +1(208)8859146; e-Mail: jshreeve@uidaho.edu;
Further Information

Publication History

Received 25 September 2002
Publication Date:
18 December 2002 (online)

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Abstract

1-Alkyl-1,2,4-triazoles were quaternized at N-4 in >98% isolated yields using polyfluoroalkyl halides under neat reaction conditions at 100-120 °C to form 1-R-4-Rf-triazolium (Taz) halides. Metathesis of these polyfluoroalkylated triazolium halides with fluorine-containing anions led to the formation of new ionic liquids, [R(Rf)Taz]+Y-.

Key words

fluoroalkylation - metathesis - fluorine-containing ionic liquids - triazolium quaternary salts

    References

  • 1 Wasserscheid P. Keim W. Angew. Chem. Int. Ed.  2000,  39:  3772 
    CrossrefPubMedGoogle Scholar
  • 2 Welton T. Chem. Rev.  1999,  99:  2071 
    CrossrefPubMedGoogle Scholar
  • 3 Hagiwara R. Ito Y. J. Fluorine Chem.  2000,  105:  221 
    CrossrefGoogle Scholar
  • 4 Bonhôte P. Dias A.-P. Papageorgiou N. Kalyanasundaram K. Grätzel M. Inorg. Chem.  1996,  35:  1168 
    CrossrefPubMedGoogle Scholar
  • 5 Seddon KR. J. Chem. Technol. Biotechnol.  1997,  68:  351 
    CrossrefGoogle Scholar
  • 6 Sheldon RA. Chem. Commun.  2001,  2399 
    CrossrefGoogle Scholar
  • 7 Merrigan TL. Bates ED. Dorman SC. Davis JH. Chem. Commun.  2000,  2051 
    CrossrefGoogle Scholar
  • 8 Larsen AS. Holbrey DJ. Tham FS. Reed CA. J. Am. Chem. Soc.  2000,  122:  7264 
    CrossrefGoogle Scholar
  • 9a Huddleston JG. Willauer HD. Swatloski RP. Visser AE. Rogers RD. Chem. Commun.  1998,  1765 
    Google Scholar
  • 9b Blanchard LA. Hancu D. Bechman EJ. Brennecke JF. Nature (London)  1999,  399:  28 
    Google Scholar
  • 9c Visser AE. Swatloski RP. Reichert WM. Griffin ST. Rogers RD. Ind. Eng. Chem. Res.  2000,  39:  3596 
    Google Scholar
  • 9d Lee KM. Lee KC. Lin IJB. Chem. Commun.  1997,  899 
    Google Scholar
  • 9e Kitazume T. Tamura K. Jiang Z. Miyake N. Kawasaki I. J. Fluorine Chem.  2002,  115:  49 
    Google Scholar
  • 9f Chauvin Y. Mußmann L. Oliver H. Angew. Chem., Int. Ed. Engl.  1995,  34:  2698 
    Google Scholar
  • 10a Fuller J. Carlin RT. Osteryoung RA. J. Electrochem. Soc.  1997,  144:  3881 
    CrossrefGoogle Scholar
  • 10b Kosmulski M. Osteryoung RA. Ciszkowska M. J. Electrochem. Soc.  2000,  147:  1454 
    CrossrefGoogle Scholar
  • 10c Matsumoto H. Matsuda T. Tsuda T. Hagiwara R. Ito Y. Miyazaki Y. Chem. Lett.  2001,  26 
    CrossrefGoogle Scholar
  • 11 Elaiwi A. Hitchcock PB. Seddon KR. Srinivasan N. Tan Y.-M. Welton T. Zora JA. J. Chem. Soc., Dalton Trans.  1995,  3467 
    CrossrefGoogle Scholar
  • 12 Schofield K. Grimmett MR. Keena BRT. Heteroaromatic Nitrogen Compounds - The Azoles   Cambridge University Press; Cambridge: 1976. 
    Google Scholar
  • 13 Potts KT. Chem. Rev.  1961,  61:  87 
    CrossrefGoogle Scholar
  • 14 Temple C. Chem. Heterocycl. Compd.  1981,  37:  1 
    Google Scholar
  • 15 Polya JB. In Comprehensive Heterocyclic Chemistry   Vol. 5:  Katritzky AR. Rees CW. Pergamon; London: 1984.  p.733 
    Google Scholar
  • 16 Vestergaard B. Bjerrum NJ. Petrushina I. Hjuler HA. Berg RW. Begtrup M. J. Electrochem. Soc.  1993,  140:  3108 
    Google Scholar
  • 17 Astleford BA. Goe GL. Keay JG. Scriven EFV. J. Org. Chem.  1989,  54:  731 
    Google Scholar
  • 18 De Keyzer R, Van Rompuy L, Dewanckele J.-M, and Monbaliu M. inventors; EP  0677790.  Chem. Abstr. 1995, 124, 71647
  • 19 Olofson RA. Kendall RV. J. Org. Chem.  1970,  35:  2246 
    Google Scholar
  • 20 Atkinson MR. Polya JB. J. Chem. Soc.  1954,  141 
    Google Scholar