Ultrasound-Accelerated Permanganate Oxidation of Amines into Carbonyl Compounds
Main Article Content
Abstract
Abstract: Potassium permanganate adsorbed on copper(II) sulfate pentahydrate has been found to be a green, efficient, and inexpensive oxidant for the transformation of amines into the corresponding ketones. The oxidation reactions were performed following two different activation methods: magnetic stirring, and ultrasound irradiation under the solvent-free or solvent conditions. Ultrasound irradiation made considerable influences on the heterogeneous reaction conversion and the product yield (> 55%) and reaction times (< 60 min).
References
References
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[3] Noureldin, N. A., Bellegarde, J. W., "A novel method. The synthesis of ketones and azobenzenes using supported permanganate", Synthesis (6), (1999) 939.
[4] Rawalay, S. S., Shechter, H., "Oxidation of primary, secondary, and tertiary amines with neutral permanganate. A simple method for degrading amines to aldehydes and ketones", J. Org. Chem. 32 (10), (1967) 3129.
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[6] Curragh, E.F., Henbest, H. B., Thomas, A., "Amine oxidation. Part VII. "Cleavage of tetra-N-substituted 1,2-diamines by manganese dioxide", J. Chem. Soc., (1960) 3559.
[7] Hashemi, M. M., Beni, Y. A., "Oxidation of alcohols and primary aliphatic amines to carbonyl compounds using sodium hypochlorite adsorbed on montmorillonite K10", J. Chem. Research(S), (2000) 224.
[8] Ratnikov, M. O., Farkas, L. E., McLaughlin, E. C., Chiou, G., Choi, H., El-Khalafy, S. H., Doyle, M. P., "Dirhodium-catalyzed phenol and aniline oxidations with T-HYDRO. Substrate scope and mechanism of oxidation", J. Org. Chem. 76 (8), (2011) 2585.
[9] Matsuo, J.-I., Kawana, A., Fukuda, Y., Mukaiyama, T., "Oxidative deamination of various primary amines to the corresponding carbonyl compounds by using N-tert-Butylphenylsulfinimidoyl chloride", Chem. Lett., (2001) 712.
[10] Mason, T. J., Lorimer, J. P., Sonochemistry: Theory, applications and uses of ultrasound in chemistry, Ellis Horwood, West Sussex, 1988.
[11] Luche, J.-L. (1998), Synthetic organic sonochemistry, Plenum press, New York.
[12] Menger, F. M., Lee, C. (1979), "Oxidations with solid potassium permanganate", J. Org. Chem. 44 (20), pp. 3446-3448.
[13] Luu, T. X. T., Christensen, P., Duus, F., Le, T. N (2008), "Microwave and ultrasound accelerated oxidation of alcohols by potassium permanganate absorbed on copper (II) sulfate pentahydrate", Synth. Commun. 38 (12), pp. 2011-2024.
[1] Padiglia, A., Medda, R., Floris, G., "Lentil seedling amine oxidase: Interaction with carbonyl reagents", Biochemistry International 28 (6), (1992) 1097.
[2] Cohen, S. G., Baumgarten, R. J., "Photoreduction of benzophenone by amines. Photochemical oxidative deamination", J. Am. Chem. Soc. 87 (13), (1965) 2996.
[3] Noureldin, N. A., Bellegarde, J. W., "A novel method. The synthesis of ketones and azobenzenes using supported permanganate", Synthesis (6), (1999) 939.
[4] Rawalay, S. S., Shechter, H., "Oxidation of primary, secondary, and tertiary amines with neutral permanganate. A simple method for degrading amines to aldehydes and ketones", J. Org. Chem. 32 (10), (1967) 3129.
[5] Barman, D. C., Saikia, P., Prajapati, D., Sandhu, J. S., "Heterogeneous permanganate oxidations. A novel method for the deamination using solid supported iron-permanganate", Synth. Commun. 32 (22), (2002) 3407.
[6] Curragh, E.F., Henbest, H. B., Thomas, A., "Amine oxidation. Part VII. "Cleavage of tetra-N-substituted 1,2-diamines by manganese dioxide", J. Chem. Soc., (1960) 3559.
[7] Hashemi, M. M., Beni, Y. A., "Oxidation of alcohols and primary aliphatic amines to carbonyl compounds using sodium hypochlorite adsorbed on montmorillonite K10", J. Chem. Research(S), (2000) 224.
[8] Ratnikov, M. O., Farkas, L. E., McLaughlin, E. C., Chiou, G., Choi, H., El-Khalafy, S. H., Doyle, M. P., "Dirhodium-catalyzed phenol and aniline oxidations with T-HYDRO. Substrate scope and mechanism of oxidation", J. Org. Chem. 76 (8), (2011) 2585.
[9] Matsuo, J.-I., Kawana, A., Fukuda, Y., Mukaiyama, T., "Oxidative deamination of various primary amines to the corresponding carbonyl compounds by using N-tert-Butylphenylsulfinimidoyl chloride", Chem. Lett., (2001) 712.
[10] Mason, T. J., Lorimer, J. P., Sonochemistry: Theory, applications and uses of ultrasound in chemistry, Ellis Horwood, West Sussex, 1988.
[11] Luche, J.-L. (1998), Synthetic organic sonochemistry, Plenum press, New York.
[12] Menger, F. M., Lee, C. (1979), "Oxidations with solid potassium permanganate", J. Org. Chem. 44 (20), pp. 3446-3448.
[13] Luu, T. X. T., Christensen, P., Duus, F., Le, T. N (2008), "Microwave and ultrasound accelerated oxidation of alcohols by potassium permanganate absorbed on copper (II) sulfate pentahydrate", Synth. Commun. 38 (12), pp. 2011-2024.