Pentylpyridinium tribromide: A vapor pressure free room temperature ionic liquid analogue of bromine

Synlett

Volumn , Issue 7, 2004, Pages 1318-1320

  Salazar, José ^a   Dorta, Romano ^a  

^a UNIVERSIDAD SIMÓN BOLÍVAR   (Venezuela)

Author keywords

Pentylpyridinium tribromide; Room temperature ionic liquid; Solvent free brominations

Indexed keywords

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; AROMATIC COMPOUND; BROMINE DERIVATIVE; KETONE DERIVATIVE; PYRIDINIUM DERIVATIVE; SOLVENT; WATER;

ARTICLE; BROMINATION; LIQUID; RECYCLING; ROOM TEMPERATURE; SOLVENT EXTRACTION; SYNTHESIS; VAPOR PRESSURE;

EID: 2942729965     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-825598     Document Type: Article

References (23)

1. Djerassi, C.; Scholz, C. R. J. Am. Chem. Soc. 1948, 70, 417.
2. Arcus, C. L.; Strauss, H. E. J. Chem. Soc. 1952, 2669.
3. (a) Banks, R. E.; Hasszeldine, R. N.; Latham, J. V.; Young, I. M. J. Chem. Soc. 1965, 594.
4. (b) Reeves, W. P.; Lu, C. V.; Schulmeier, B.; Jonas, L.; Hatlevik, O. Synth. Commun. 1998, 28, 499.
5. Ali, S. I.; Nikalje, M. D.; Sudalai, A. Org. Lett. 1999, 1, 705.
6. (a) Tanaka, K.; Shiraishi, R.; Toda, F. J. Chem. Soc., Perkin Trans. 1 1999, 3069.
7. Apart from PHP, ammonium tribromides are widely used brominating agents, see for example:. (b) Buckles, R. E.; Popov, A. I.; Zelezny, W. F.; Smith, R. J. J. Am. Chem. Soc. 1951, 73, 4525. (c) Avramoff, M.; Weiss, J.; Schaechter, O. J. J. Org. Chem. 1963, 28, 3256. (d) Kajigaeshi, S.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans. 1 1990, 897. (e) Muathen, H. A. J. Org. Chem. 1992, 57, 2740.
8. Apart from PHP, ammonium tribromides are widely used brominating agents, see for example:. (b) Buckles, R. E.; Popov, A. I.; Zelezny, W. F.; Smith, R. J. J. Am. Chem. Soc. 1951, 73, 4525. (c) Avramoff, M.; Weiss, J.; Schaechter, O. J. J. Org. Chem. 1963, 28, 3256. (d) Kajigaeshi, S.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans. 1 1990, 897. (e) Muathen, H. A. J. Org. Chem. 1992, 57, 2740.
9. Apart from PHP, ammonium tribromides are widely used brominating agents, see for example:. (b) Buckles, R. E.; Popov, A. I.; Zelezny, W. F.; Smith, R. J. J. Am. Chem. Soc. 1951, 73, 4525. (c) Avramoff, M.; Weiss, J.; Schaechter, O. J. J. Org. Chem. 1963, 28, 3256. (d) Kajigaeshi, S.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans. 1 1990, 897. (e) Muathen, H. A. J. Org. Chem. 1992, 57, 2740.
10. Apart from PHP, ammonium tribromides are widely used brominating agents, see for example:. (b) Buckles, R. E.; Popov, A. I.; Zelezny, W. F.; Smith, R. J. J. Am. Chem. Soc. 1951, 73, 4525. (c) Avramoff, M.; Weiss, J.; Schaechter, O. J. J. Org. Chem. 1963, 28, 3256. (d) Kajigaeshi, S.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans. 1 1990, 897. (e) Muathen, H. A. J. Org. Chem. 1992, 57, 2740.
11. Chiappe, C.; Capraro, D.; Conte, V.; Pieraccini, D. Org. Lett. 2001, 3, 1061.
12. (a) Bates, E. D.; Mayton, R. D.; Ntai, I.; Davis, J. H. Jr. J. Am. Chem. Soc. 2002, 124, 926.
13. (b) Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Mayton, R.; Sheff, S.; Wierzbicki, A.; Davis, J. H. Jr.; Rogers, R. D. Chem. Commun. 2001, 135.
14. (c) Bartolini, O.; Bottai, M.; Chiappe, C.; Conte, V.; Pieraccini, D. Green Chem. 2002, 4, 621.
15. For a synthesis of 1, see: Zhu, Z.; Ching, C.; Carpenter, K.; Xu, R.; Selvaratnam, S.; Hosmane, N. S.; Maguire, J. A. Appl. Organomet. Chem. 2003, 17, 346. Bromide 1 is a white hygroscopic solid that melts in humid air affording an 'RTIL' although, strictly speaking, it is not.
16. 3: C, 30.80; H, 4.14; N, 3.59. Found: C, 30.95; H, 4.11; N, 3.71.
17. (a) Barnes, H. A.; Hutton, J. F.; Walters, K. An Introduction to Rheology, Elsevier: Amsterdam, Oxford, New York, Tokyo, 1989.
18. -1 Pa s, respectively.
19. Similar examples that demonstrate the complete elimination of residual vapor pressure of strong acids in functional RTIL are: (a) Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, J. H. Jr. J. Am. Chem. Soc. 2002, 124, 5962. (b) Susan, M. A. B. H.; Noda, A.; Mitsushima, S.; Watanabe, M. Chem. Commun. 2003, 938.
20. Similar examples that demonstrate the complete elimination of residual vapor pressure of strong acids in functional RTIL are: (a) Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, J. H. Jr. J. Am. Chem. Soc. 2002, 124, 5962. (b) Susan, M. A. B. H.; Noda, A.; Mitsushima, S.; Watanabe, M. Chem. Commun. 2003, 938.
21. 4, filtered and left for 5 min under high vacuum to remove traces of bromine leaving a colorless liquid (2.60 g, 84%). Spectroscopic data corresponded to a pure sample of 1,2-dibromocyclohexane.
22. For examples, see: (a) Smith, M. B.; Guo, L. C.; Okey, S.; Stenzel, J.; Yanella, J.; LaChapelle, E. Org. Lett. 2002, 4, 2321. (b) Bora, U.; Bose, G.; Chaudhuri, M. K.; Dhar, S. S.; Gopinath, R.; Khan, A. T.; Patel, B. K. Org. Lett. 2000, 2, 247.
23. For examples, see: (a) Smith, M. B.; Guo, L. C.; Okey, S.; Stenzel, J.; Yanella, J.; LaChapelle, E. Org. Lett. 2002, 4, 2321. (b) Bora, U.; Bose, G.; Chaudhuri, M. K.; Dhar, S. S.; Gopinath, R.; Khan, A. T.; Patel, B. K. Org. Lett. 2000, 2, 247.