Green Oxidation of Organic Compounds: Manganese Sulphate/Oxone®/Water
DOI:
https://doi.org/10.29356/jmcs.v51i4.1284Keywords:
Green oxidation, aromatic compounds, managanese sulphate, oxone, amines, alcohols, benzylic groupsAbstract
Abstract. We present a methodology for the oxidation of aromatic organic compounds based on manganese sulphate, Oxone® and water. The proposed method, which involves mild reaction conditions, was shown to produce various functional groups of interest in good yield, when applied to amines, alcohols and benzylic groups. This method has several advantageous characteristics, including lowcost reagents, aqueous reaction conditions, moderate temperatures, and short reaction times.
Resumen. Presentamos una nueva metodología para la oxidación de compuestos aromáticos basada en sulfato de manganeso, Oxone® y agua. El método propuesto, el cual involucra condiciones de reacción suaves, produce distintos grupos funcionales de interés en buenos rendimientos, cuando se aplica a aminas, alcoholes y metilos bencílicos. Este método tiene varias ventajas, incluyendo bajo costo de reactivos, medio acuoso, temperaturas moderadas y tiempos cortos de reacción.
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References
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2. a) Jefford, C. W.; Wang, Y. J. Chem. Soc., Chem. Commun. 1988, 634-635. b) Oyster, L.; Adkins, H. J. Am. Chem. Soc. 1921, 43, 208-210. c) Schaeffer, J. R.; Snoddy, A. O. Organic Syntheses. 1963. Coll. Vol. 4, 19-21.
3. a) Ho, T. L. Synthesis 1973, 347-353. b) Bowden, K.; Heilbron, I. M.; Jones, E. R. H.; Weedon, B. C. L. J. Chem. Soc. 1946, 39-45. c) Hayakawa, Y.; Uchiyama, M.; Noyori, R. Tetrahedron Lett. 1986, 27, 4195-4196. d) Postowsky, J.; Lugowkin, B. P. Chem. Ber. 1935, 68, 852-856.
4. a) Carmelli, M.; Rozen, S. J. Org. Chem. 2006, 71, 4585-4589. b) Jain, S. L.; Sain, B. Angew. Chem. Int. 2003, 42, 1265-1267. c) Suresh, S.; Joshep, R.; Jayachandran, B. Tetrahedron 1995, 51, 11305-11318.
5. a) Fatiadi, A. J. Synthesis 1976, 65-104. b) Fatiadi, A. J. Synthesis 1976, 133-167. c) Gritter, R. J.; Wallace, T. J. J. Org. Chem. 1959, 24, 1051-1056. d) Sondheimer, F.; Amendolla, C.; Rosenkraz, E. J. Am. Chem. Soc. 1953, 75, 5932-5935. e) Lane, B. S.; Vogt, M; DeRose, V. J.; Burgess, K. J. Am. Chem. Soc. 2002, 124, 11946- 11954.
6. Tallec, A. Electrochimie Organique. Synthéses et Mecanismes. 1985, 95-97. Ed Masson. Paris.
7. a) Webb, K. S.; Ruszkay, S. J. Tetrahedron 1998, 54, 401-410. b) Varma, R. S.; Dahiya, R. K. Molecules 1998, 282-285. c) Curini, M.; Epifanio, F.; Marcotullio, M. C.; Rosati, O. Synlett 1999, 6, 777-779. d) He, W. Synlett 2006, 20, 3548-3549.
8. a) Haijipur, A. R.; Mallakpour, S. E.; Adibi, H. Chem. Lett. 2000, 5, 460-461. b) Deasi, U. V.; Pore, D.M.; Tamhankar, B. V.; Jaghav, S. A.; Wadgaonkar, P. P. Tetrahedron Lett. 2006, 47, 8559-8561. c) Adams, J. Am. Chem. Soc. 1924, 46, 1889-1896. d) Vogel, A. I.; Practical Organic Chemistry. 1959 (Longmans, London, 3° ed,) 755-757.
9. a) Suresh, S.; Joshep, R.; Jayachandran, B. Tetrahedron 1995, 51, 11305-11318. b) Sharma, V. B.; Jain, S. L.; B. Sain. Tetrahedron
Lett. 2003, 44, 3235-3237. e) Clarke, H. T.; Taylor, E. R. Organic Syntheses 1923, 3, 91-92.
10. a) A. Defoin, A. Synthesis 2004, 5, 706-710. b) Siraki, A. G.; Chan, T. S.; Galati, G.; Teng, S.; O’Brien, P. Drug Metabolism Reviews 2002, 34, 549 – 564 c) Eyer, P.; Gallemann, D. The Chemistry of Amino, Nitroso, Nitro and Related Groups 2003. John Wiley & Sons, Ltd. Israel. 999-1039.
11. a) Pratt, E. F.; Van de Castle, J. F. J. Org. Chem. 1961, 26, 2973-2975. b) Hajipour, A. R.; Rafiee, F. Synth. Commun. 2006, 36, 2563-2568. c) Zabrowski, D. L.; Moorman, A. E.; Beck, K. R. Tetrahedron Lett. 1988, 29, 4501-4504.
12. a) Niedzielski, N. J. Am. Chem. Soc. 1941, 63, 1462-1463. b) Sisti, A.; Burgmaster, J.; Fudim, M. J. Org. Chem. 1962, 27, 279-281.
13. a) Loitz, C.; Looper, R.; Peterson, E. Tetrahedron Lett. 1981, 22, 2605-2608. b) Harmata, M.; Hong, X.; Barnes, C. Synthesis 1987, 8, 723-724. c) Kimachi, T.; Takemoto, Y. Tetrahedron Lett. 2004, 45, 5109- 5112.
14. a) Campaigne, E.; Archer, W. L. Organic Syntheses 1963 Coll. Vol. 4, 331-333. b) Vilsmeier, A.; Haack, A. Chem. Ber. 1927, 60, 119-122. c) Adams, R.; Coleman, G. H. Org. Syntheses 1941 Coll. Vol. 1, 214-217.
15. http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng, accessed in June, 2007.
16. a) Prestch, E.; Bühlmann, P.; Affolter, C.; Herrera, A.; Martínez, R. Determinación Estructural de Compuestos Orgánicos 2005. Ed. Masson. España.
17. The Merck Index. Whitehouse Station, New Jearsy. USA. 2001.
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2020-07-24
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