Synthesis and Characterization of a New Oxidation Reagent: Tetrahexylammonium Chlorochromate, (C6H13)4N[CrO3Cl]
Behnam Koohestani,1 Zahra Javanshir,2 Shahriare Ghammamy,3* Kheyrollah Mehrani,2 Hamid Afrand,2 and Lotfali Saghatforoush4
1 Department of Chemical Engineering, Faculty of Engineering, Islamic Azad University, Arak Branch, Arak, Iran.
2 Department of Chemistry, Faculty of Science, Islamic Azad University, Ardebil Branch, Ardebil, Iran.
3 Department of Chemistry, Faculty of Science, Imam Khomeini International University, Ghazvin, Iran. *Responsible author: shghamami@ikiu.ac.ir or shghamamy@yahoo.com.
4 Department of Chemistry, Payam Noor University (PNU), Khoy, Iran.
]]>Recibido el 22 de enero de 2008
Aceptado el 24 de abril de 2008
Abstract
Tetrahexylammonium chlorochromate, THACC, is a new compound, more efficient, and has certain advantages over similar oxidizing agents, in terms of the amount of oxidant, short reaction times, and high yields. This reagent is suitable for oxidizing various primary and secondary alcohols to their corresponding carbonyl compounds. The facile oxidation of triphenylphosphine to triphenylphosphine oxide by this reagent in acetonitrile provides a clear–cut example indicating an oxygen atom transfer mechanism.
Key words: Chromium(VI), Tetrahexylammonium chlorochromates, Oxidation, Organic substrate, Alcohols.
Resumen
Clorocromato de tetrahexilamonio, THACC, es un nuevo compuesto, más eficiente, y tiene ciertas ventajas sobre agentes oxidantes similares, en términos de la cantidad del oxidante, tiempos de reacción más cortos y elevados rendimientos. Este reactivo es capaz de oxidar varios alcoholes primarios y secundarios a los compuestos carbonílicos correspondientes. La fácil oxidación de trifenilfosfina al óxido de trifenilfosfina por parte de este reactivo en acetonitrilo proporciona un ejemplo de mecanismo de transferencia de átomo de oxígeno.
]]> Palabras clave: Cromo(VI), clorocromatos tetrahexilamónicos, oxidación, substrato orgánico, alcoholes.
DESCARGAR ARTÍCULO EN FORMATO PDF
Acknowledgements
The authors would like to thank Dr. Gh. Rezaei Behbahani, M.R. Gouya, and Mr. K. Mohammady for valuable discussions.
References
1. Lan, Y.; Deng, B.; Kim, C.; Thornton, E. C.; Xu, H.; Environ. H. Sci. Technol. 2005, 39, 2087–2094. [ Links ]
]]>2. a) Losi, M. E.; Amrhein, C.; Frankenberger, W. T. Rev. Environ. Contam. Toxicol. 1994, 136, 91–121. [ Links ] b) Viamajala, S.; Peyton, B. M.; Sani, R. K.; Apel, W. A.; Petersen, J. N. Biotechnol. Prog. 2004, 20, 87–95. [ Links ]
3. Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis, Wiley, New York. 1967–1984, 1–11. [ Links ]
4. Bhattacharjee, M. N.; Chaudhuri, M. K.; Dasgupta, H. S.; Roy, N. Synthesis 1982, 588–590. [ Links ]
5. Shirini, F.; Mohammadpoor–Baltork, I.; Hejazi, Z.; Heravi, P. Bull. Korean Chem. Soc. 2003, 24, 517–518. [ Links ]
6. Murugesan, V.; Pandurangan, A. Indian J. Chem. 1992, 31B, 377–379. [ Links ]
7. Hajipour, A. R.; Khazdooz, L.; Ruoho, A. E. J. Iranian Chem. Soc. 2005, 2, 315–318. [ Links ]
8. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 20, 399–402. [ Links ]
9. Javanthi, G.; Vijayakumar, G.; Elango, K. P.; J. Serb. Chem. Soc. 2002, 67, 803–808. [ Links ]
10. Srinivasan, R.; Stanley, P.; Balasubramanian, K. Synth. Commun. 1997, 27, 2057–2064. [ Links ]
11. Corey, J.; Fleet, G. W. J. Tetrahedron Lett. 1973, 14, 4499–4501. [ Links ]
12. Ghammami, S.; SeyedSadjadi, S. A.; J. Serb. Chem. Soc. 2005, 70, 1243–1248. [ Links ]
13. Mamaghani, M.; Shirini, F.; Parsa, F. Russ J Org Chem. 2002, 38, 1113–1115. [ Links ]
14. Ghammamy, S.; Hashemzadeh, A. Bull. Korean Chem. Soc. 2004, 25, 1277–1279. [ Links ]
15. Lee, D. G.; Spitzer, U. A. J. Org. Chem. 1970, 35, 3589–3590. [ Links ]
16. Robertson, G. R. Organic Synthesis. Coll. Vol. 1; p. 138. [ Links ]
17. Kassaee, M. K.; Mahjoub, A. R.; Ghammami, S. Tetrahedron Lett. 2003, 44, 4555–4557. [ Links ]
18. Kassaee, M. Z.; Sayyed–Alangi, S. Z.; Sajjadi–Ghotbabadi, H. Molecules 2004, 9, 825–829. [ Links ]
19. Nakamoto, K. Inorganic Compounds, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Vol. 1. Part II, Third Edition, Wiley, New York, 1978, p. 140. [ Links ]
]]>