Syntheses of 1-alkyl-1,2,4-triazoles and the formation of quaternary 1-alkyl-4-polyfluoroalkyl-1,2,4-triazolium salts leading to ionic liquids

Journal of Organic Chemistry

Volumn 67, Issue 26, 2002, Pages 9340-9345

  Mirzaei, Yousef R ^a   Twamley, Brendan ^a   Shreeve, Jean'ne M ^a  

^a UNIVERSITY OF IDAHO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IONIC LIQUED; ORTHORHOMBIC SPACE GROUP;

ALKYLATION; CRYSTALLIZATION; FLUORIDE MINERALS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY ANALYSIS;

SYNTHESIS (CHEMICAL);

1,2,4 TRIAZOLE DERIVATIVE; ALKYL GROUP; FLUORINE DERIVATIVE; HALIDE; INORGANIC SALT; IODINE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CRYSTAL STRUCTURE; CRYSTALLIZATION; FLUORINATION; LIQUID; PURIFICATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TEMPERATURE;

EID: 0037184838     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026350g     Document Type: Article

References (32)

1. (a) Vestergaard, B.; Bjerrum, N. J.; Petrushina, I.; Hjuler, H. A.; Berg, R. W.; Begtrup, M. J. Electrochem. Soc. 1993, 140, 3108-3113.
2. (c) Astleford, B. A.; Goe, G. L.; Keay, J. G.; Scriven, E. F. V. J. Org. Chem. 1989, 54, 731-732.
3. (a) Storr, R. C. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F., Eds.; Pergamon: New York, 1996; Vol. 4, pp 127-164.
4. (b) Katritzky, A. R.; Pozharskii, A. F. In Handbook Of Heterocyclic Chemistry; Pergamon/Elsevier Science, Ltd.: New York, 2000; pp 91-140 and 367-474.
5. (c) e.g.: Dalvie, D. K.; Kalgutkar, A. S.; Khojasteh-Bakht, C.; Obach, R. S.; O'Donnell, J. P. Chem. Res. Toxicol. 2002, 15, 269-299 and references therein.
6. (d) Olofson, R. A.; Kendall, R. V. J. Org. Chem. 1970, 35, 2246-2248.
7. Seddon, K. R. J. Chem. Technol. Biotechnol. 1997, 68, 351-356.
8. (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083.
9. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
10. (c) Sheldon, R. A. J. Chem. Soc., Chem. Commun. 2001, 2399-2407.
11. (d) Hagiwara, R.; Ito, Y. J. Fluorine Chem. 2000, 105, 221-227.
12. (a) Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. J. Chem. Soc., Chem. Commun. 1998, 1765-1766.
13. (b) Blanchard, L. A.; Nancu, E. J.; Bechman, E. J.; Brennecke, J. F. Nature 1999, 399, 28-29.
14. (c) Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Griffin, S. T.; Rogers, R. D. Ind. Eng. Chem. Res. 2000, 39, 3596-3604.
15. (d) Larsen, A. S.; Holbrey, J. D.; Tham, F. S.; Reed, C. A. J. Am. Chem. Soc. 2000, 122, 7264-7272.
16. (e) Lee, K. M.; Lee, K. C.; Lin, I. J. B. J. Chem. Soc., Chem. Commun. 1997, 899-900.
17. (f) Kitazume, T.; Tamura, K.; Jiang, Z.; Miyake, N.; Kawasaki, I. J. Fluorine Chem. 2002, 115, 49-53.
18. (g) Chauvin, Y.; Mussmann, L.; Oliver, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2698-2700.
19. (a) Fuller, J.; Carlin, R. T.; Osteryoung, R. A. J. Electrochem. Soc. 1997, 144, 3881-3886.
20. (b) Kosmulski, M.; Osteryoung, R. A.; Ciszkowska, M. J. Electrochem. Soc. 2000, 147, 1454-1458.
21. (c) Matsumoto, H.; Matsuda, T.; Tsuda, T.; Hagiwara, R.; Ito, Y.; Miyazaki, Y. Chem. Lett. 2001, 26-27.
22. Grimmett, M. R.; Keene , B. R. T. In Heteroaromatic Nitrogen Compounds: The Azoles; Schofield, K., Ed.; Cambridge University Press: Cambridge, 1976; p 1921.
23. Potts, K. T. Chem. Rev. 1961, 61, 87-127.
24. Gupta, R. R.; Kumar, M.; Gupta, V. Heterocyclic Chemistry II; Springer: New York, 1999; pp 492-512 and references therein.
25. Bonhôte, P.; Dias, A. P.; Papageorgiou, N.; Kalyanasundaram, K.; Grätzel, M. Inorg. Chem. 1996, 35, 1168-1178.
26. Elaiwi, A.; Hitchcock, P. B.; Seddon, K. R.; Srinivasan, N.; Tan, Y-. M.; Welton, T.; Zora, J. A. J. Chem. Soc., Dalton Trans. 1995, 3467-3472.
27. Atkinson, M. R.; Polya, J. B. J. Chem. Soc. 1954, 141-145.
28. Hope, H. Prog. Inorg. Chem. 1995, 41, 1-3.
29. SMART: Version 5.625, Bruker Molecular Analysis Research Tool; Bruker AXS: Madison, WI, 2001.
30. SAINTPlus: Version 6.22, Data Reduction and Correction Program; Bruker AXS: Madison, WI, 2001.
31. Sheldrick, G. M. SADABS: Version 2.01, An Empirical Absorption Correction Program; Bruker AXS: Madison, WI, 2001.
32. Sheldrick, G. M. SHELXTL: Version 6.10, Structure Determination Software Suite; Bruker AXS: Madison, WI, 2001.