Oxidation of Some Organic Diols with Trialkylammonium Fluorochromates(VI), R3NH[CrO3F], (R= CH3, C2H5, C3H7 and C4H9) at Room Temperature and Under Microwave Condition
Shahriar Ghammamy,1, 2* Samira Khorsandtabar,1 Ali Moghimi,3 and Hajar Sahebalzamani4
1 Department of Chemistry, Islamic Azad University, Takestan Branch, Takestan, Iran. *Responsible author: shghamami@yahoo.com or shghamamy@yahoo.com.
2 Department of Chemistry, Faculty of Science, Imam Khomeini International University, Qazvin, Iran.
3 Department of Chemistry, Islamic Azad University, Varamin Branch, Varamin, Iran.
4 Departments of Chemistry, Faculty of Science, Islamic Azad University, Ardabil Branch, Ardabil, Iran.
]]>Received February 18, 2009
Accepted June 16, 2009
Abstract
A mild and efficient method for the mono–oxidation of diols to the corresponding hydroxyaldehydes with trialkylammonium fluorochromates(VI), R3NH[CrO3F] (R= CH3, C2H5 C3H7 and C4H9), in solution at room temperature, and in solution under microwave radiation, is reported. The easy procedure, simple work–up, short reaction times, and excellent yields are advantages of these reagents.
Keywords: Trialkylammonium fluorochromates(VI); oxidants; oxidation; diols; microwave; room temperature.
Resumen
Se describe un método eficiente y suave para la mono–oxidación de dioles a los hidroxialdehidos correspondientes con fluorocromatos(VI) de trialquilamonio, R3NH[CrO3F] (R = CH3, C2H5, C3H7 y C4H9), en solución a temperatura ambiente y en solución bajo irradiación de microondas. La facilidad del procedimiento y la sencillez de la extracción del producto, así como de los tiempos de reacción cortos y los rendimientos elevados, son una muestra de las ventajas de estos reactivos.
]]> Palabras clave: Fluorocromatos(VI) de trialquilamonio; oxidantes; oxidación; dioles; microondas; temperatura ambiente.
DESCARGAR ARTÍCULO EN FORMATO PDF
Acknowledgements
The author thanks Dr. A. R. Mahjoub, Mr. M. K. Mohammady and Mr. S. Bagi for valuable discussion.
References
1. a) Bhandari, A.; Sharma, P. K.; Banerji, K. K. Indian J. Chem, 2001, 40A, 470–474 b) Ghammamy, [ Links ] S.; Moghimi, A.; Kohestani, B. Fluorine Notes J. 2008, 59. [ Links ]
2. O'Brien, B. A. Part I: Reactions of potassium dihydrogen–phosphide and potassium diphenylphosphide with organic carbonyl compounds. Part II: Oxidation of primary and secondary alcohols by potassium chlorochromate( VI). School of Chemistry and Biochemistry Thesis and Dissertations, Georgia Tech. 1980. [ Links ]
3. Littler, J. S. Tetrahedron 1971, 27, 81–91. [ Links ]
4. Trahanovsky, W. S.; Young, L. H.; Bierman, M. H. J. Org. Chem. 1969, 34, 869–871. [ Links ]
5. Yu, H.; Guo, F. Huaxue Shiji 2005, 27, 186. [ Links ]
6. Takahashi, N.; Katsuki, O. Decomposition of ethylene glycol by the combined use of ozone oxidation and electrolytic methods, Natl. Res. Inst. Pollut. Resour., Sukuba, Japan. Ozone: Science & Engineering, 1990, 12, 115–31. [ Links ]
7. Mohammadi, M. K.; Ghammamy, S.; Imanieh, H. Bull. Chem. Soc. Ethiop. 2008, 22, 449–452. [ Links ]
8. Seyedsajadi, S. A.; Ghammamy, S. Indian J. Chem. Sec. B, 2006, 45, 564–567. [ Links ]
9. Ghammamy, S.; Mazareey, M. J. Serb. Chem. Soc. 2005, 70, 687–693. [ Links ]
10. Ghammamy, S.; Hashemzadeh, A. Bull. Korean Chem. Soc. 2004, 25, 1277–1279. [ Links ]
11. Meenahshisundaram, S.; Soctaungam, R. Collect. Czech. Chem. Commun, 2001, 66, 877–896. [ Links ]
12. Corey, E. J.; Boger, D. L. Tetrahedron Lett. 1978, 19, 2461–2464. [ Links ]
13. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 20, 399–402. [ Links ]
14. Bhattacharjee, M. N.; Chaudhuri, M. K.; Dasgupta, H. S.; Roy, N. Synthesis 1982, 588–590. [ Links ]
15. Guziec, F. S.; Luzzio, F. A. Synthesis, 1980, 691–694. [ Links ]
16. Ghammamy, S.; Hashemzadeh, A. Bull. Korean Chem. Soc. 2004, 25, 1277–1279. [ Links ]
17. Mahjoub, A. R.; Ghammami, S.; Kassaee, M. Z. Tetrahedron Lett. 2003, 44, 4555– 4557. [ Links ]
18. akamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, Third Edition, John Wiley & Sons: New York, 1978, Vol. 1 pp 140–150. [ Links ]
]]>