N-Ethylbenzylammonium Fluorochromate (VI) Adsorbed on Silica Gel, a Mild and Selective Heterogeneous Reagent
DOI:
https://doi.org/10.29356/jmcs.v54i4.914Keywords:
N-ethylbenzylammonium Fluorochromate (VI); Heterogeneous Oxidant; Alcohols; Aldehyde; Ketone.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-ethylbenzylammonium fluorochromate (VI) adsorbed on silica gel is inert to aldehydes, ketones, oximes, thiols, sulfides, phenols, pyrans, trimethylsilanes, malonates and thioacetamides.
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References
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3. Bhattacharjee, M. N.; Chaudhuri, M. K.; Dasgupta, H. S.; Roy N.; Khathing, D. T. Synthesis 1982, 588-590.
4. Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 16, 2647-2650.
5. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 20, 399-402.
6. Murugesan, V.; Pandurangan, A. Indian J. Chem. 1992, 31B, 377-379.
7. Srinivasan; R.; Balasubramanian, K. Synth. Commun. 2000, 30(24), 4397-4404.
8. Srinivasan, R.; Stanley, P.; Balasubramanian, K. Synth. Commun. 1997, 27, 2057-2064.
9. Bora, U.; Chaudhuri, M. K. Tetrahedron 2001, 57, 2445-2448.
10. a) Tajbakhsh, M.; Hosseinzadeh, R.; Yazdani-Niaki, M. J. Chem. Res. 2002, 508-510; b) Hosseinzadeh, R.; Tajbakhsh, M.; Shakoori, A.; Yazdani-Niaki, M. Monatsh. Chem. 2004, 135, 1243-1249.
11. a) Hosseinzadeh, R.; Tajbakhsh, M.; Yazdani-Niaki, M. Tetrahedron Lett. 2002, 43, 9413-9416; b) Tajbakhsh, M.; Hosseinzadeh, R.; Shakoori, A. Tetrahedron Lett. 2004, 45, 1889- 1893.
12. Mahjob, A. R.; Ghammami, S.; Kassaee, M. K. Tetrahedron Lett. 2003, 44, 4555-4557.
13. Ghammami, S.; Seyed Sajadi, S. A. J. Serb. Chem. Soc. 2005, 70, 1243-1248.
14. a) Malani, N.; Baghmar, S. P.; Sharma, P. K. Indian J. Chem. 2008, 47A, 1373-1376; b) Choudhary, A.; Agarwal, S.; Sharma, V. Indian J. Chem. 2009, 48A, 362-366; c) Shiekh, H. N.; Sharma, M.; Hussain, M.; Kolsorta, B. L. Oxid. Commun. 2005, 28, 887-893; d) Bishnoi, G.; Malani, N.; Sindal, R. S.; Sharma, P. K. J. Indian Chem. Soc. 2007, 84, 892-896.
15. Kassaee, M. Z.; Hattami, M.; Moradi, M. Acta Chim. Slov. 2004, 51, 743-750.
16. Ghammamy, S.; Hashemzadeh, A. Bull. Korean Chem. Soc. 2004, 25, 1277-1279.
17. a) Sivamurugan, V.; Abraham, Rajkumar G.; Arabindo, B.; Murugesan, V. Indian J. Chem. 2005, 44B, 144-147; b) Dharmaraja, J.; Krishnasamy, K.; Shanmugam, M. E-J. Chemistry 2008, 5, 754-760.
18. Ravdeep, K.; Neelam, S.; Vinita, S. Indian J. Chem. 2006, 45A, 2441-2445.
19. Kassaee, M. Z.; Sayyed-Alangi, S. Z.; Sajjadi-Ghotbabadi, H. Molecules 2004, 9, 825-829.
20. Sayyed-Alangi, S. Z.; Sajjadi-Ghotbabadi, H.; Baei, M. T.; Naderi, S. E-J. Chemistry accepted.
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; b) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop M. A.
J. Med. Chem. 1994, 37, 1385-1401; c) Fruchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17-42; d) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527- 4554; e) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173; f) Thompson, L.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
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.
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2019-06-05
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