Article

 

N–Ethylbenzylammonium Fluorochromate (VI) Adsorbed on Silica Gel, a Mild and Selective Heterogeneous Reagent

 

S. Zahra Sayyed–Alangi* and Mohammad T. Baei

 

Islamic Azad University, Azadshahr Branch, Department of Chemistry, Azadshahr, Golestan, Iran. Tel. (+98)1722240194, Fax. (+98)1746724003. zalangi_szalangi@yahoo.com

 

Received July 12, 2010.
Accepted September 8, 2010.

 

Abstract

A mild and selective method for the oxidation of primary and secondary alcohols to their corresponding aldehydes and ketones with N–ethylbenzylammonium fluorochromate (VI), EBAFC, is reported. Stability, reaction rate, ease of work–up and efficiency of the EBAFC are considerably increased upon its adsorption on silica gel. The N–emylbenzylammonium fluorochromate (VI) adsorbed on silica gel is inert to aldehydes, ketones, oximes, thiols, sulfides, phenols, pyrans, trimethylsilanes, malonates and thioacetamides.

Keywords: N–ethylbenzylammonium Fluorochromate (VI), Heterogeneous Oxidant, Alcohols, Aldehyde, Ketone.

 

Resumen

Se describe un método suave y selectivo para la oxidación de alcoholes primarios y secundarios a sus aldehidos y cetonas correspondientes, con el fluorocromato de N–etil bencil amonio (FCEBA). La estabilidad, la velocidad de la reacción, la facilidad en el trabajo de la reacción y la eficiencia del FCEBA se incrementan considerablemente cuando este reactivo se adsorbe sobre gel de sílice. El fluorocromato de N–etil bencil amonio (VI) adsorbido sobre gel de sílice es inerte con aldehidos, cetonas, oximas, tioles, sulfuros, fenoles, piranos, trimetilsilanos, malonatos y tioacetamidas.

Palabras clave: Fluorocromato de N–etil bencil amonio (VI), Oxidantes heterogéneos, Alcoholes, Aldehídos, Cetonas.

 

DESCARGAR ARTÍCULO EN FORMATO PDF

 

References

1. Ghammami, S.; Khorsandtabar, S.; Moghimi, A.; Sahebalzamani, H. J. Mex. Chem. Soc. 2009, 53, 41–43.         [ Links ]

2. Bhattacharjee, M. N.; Chaudhuri, M. K.; Purkayastha, S. Tetrahedron 1987, 43, 5389–5392.         [ Links ]

3. Bhattacharjee, M. N.; Chaudhuri, M. K.; Dasgupta, H. S.; Roy N.; Khathing, D. T. Synthesis 1982, 588–590.         [ Links ]

4. Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 16, 2647–2650.         [ Links ]

5. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 20, 399–402.         [ Links ]

6. Murugesan, V.; Pandurangan, A. Indian J. Chem. 1992, 31B, 377379.         [ Links ]

7. Srinivasan; R.; Balasubramanian, K. Synth. Commun. 2000, 30(24), 4397–4404.         [ Links ]

8. Srinivasan, R.; Stanley, P.; Balasubramanian, K. Synth. Commun. 1997, 27, 2057–2064.         [ Links ]

9. Bora, U.; Chaudhuri, M. K. Tetrahedron 2001, 57, 2445–2448.         [ Links ]

10. a) Tajbakhsh, M.; Hosseinzadeh, R.; Yazdani–Niaki, M. J. Chem. Res. 2002, 508–510;         [ Links ] b) Hosseinzadeh, R.; Tajbakhsh, M.; Shakoori, A.; Yazdani–Niaki, M. Monatsh. Chem. 2004, 135, 1243–1249.         [ Links ]

11. a) Hosseinzadeh, R.; Tajbakhsh, M.; Yazdani–Niaki, M. Tetrahedron Lett. 2002, 43, 9413–9416;         [ Links ] b) Tajbakhsh, M.; Hosseinzadeh, R.; Shakoori, A. Tetrahedron Lett. 2004, 45, 18891893.         [ Links ]

12. Mahjob, A. R.; Ghammami, S.; Kassaee, M. K. Tetrahedron Lett. 2003, 44, 4555–4557.         [ Links ]

13. Ghammami, S.; Seyed Sajadi, S. A. J. Serb. Chem. Soc. 2005, 70, 1243–1248.         [ Links ]

14. a) Malani, N.; Baghmar, S. P.; Sharma, P. K. Indian J. Chem. 2008, 47A, 1373–1376;         [ Links ] b) Choudhary, A.; Agarwal, S.; Sharma, V. Indian J. Chem. 2009, 48A, 362–366;         [ Links ] c) Shiekh, H. N.; Sharma, M.; Hussain, M.; Kolsorta, B. L. Oxid. Commun. 2005, 28, 887–893;         [ Links ] d) Bishnoi, G.; Malani, N.; Sindal, R. S.; Sharma, P. K. J. Indian Chem. Soc. 2007, 84, 892–896.         [ Links ]

15. Kassaee, M. Z.; Hattami, M.; Moradi, M. Acta Chim. Slov. 2004, 51, 743–750.         [ Links ]

16. Ghammamy, S.; Hashemzadeh, A. Bull. Korean Chem. Soc. 2004, 25, 1277–1279.         [ Links ]

17. a) Sivamurugan, V.; Abraham, Rajkumar G.; Arabindo, B.; Murugesan, V. Indian J. Chem. 2005, 44B, 144–147;         [ Links ] b) Dharmaraja, J.; Krishnasamy, K.; Shanmugam, M. E–J. Chemistry 2008, 5, 754–760.         [ Links ]

18. Ravdeep, K.; Neelam, S.; Vinita, S. Indian J. Chem. 2006, 45A, 2441–2445.         [ Links ]

19. Kassaee, M. Z.; Sayyed–Alangi, S. Z.; Sajjadi–Ghotbabadi, H. Molecules 2004, 9, 825–829.         [ Links ]

20. Sayyed–Alangi, S. Z.; Sajjadi–Ghotbabadi, H.; Baei, M. T.; Naderi, S. E–J. Chemistry accepted.         [ Links ]

21. a) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1233–1251;         [ Links ] b) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop M. A. J. Med. Chem. 1994, 37, 1385–1401;         [ Links ] c) Fruchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17–42;         [ Links ] d) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 45274554;         [ Links ] e) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135–8173;         [ Links ] f) Thompson, L.; Ellman, J. A. Chem. Rev. 1996, 96, 555–600.         [ Links ]

22. a) Cheng, Yu–Shia; Liu, Wen–Liang; Chen, Shu–hsia. Synthesis 1980, 223–224; b) Sanjay, B.; Subrata, K. C. Tetrahedron 2003, 5, 3493–3498.         [ Links ]