Abstract
The Mn(acac)3—RCN—CCl4 system was found to be efficient for the oxidation of secondary alcohols into the corresponding ketones in 80—93% yields. The oxidation proceeds through the formation of alkyl hypochlorites, which are generated from CCl4 and the alcohols in the presence of the Mn(acac)3—RCN catalytic system (R = Me, Et, and Ph).
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C. Jrwin and G. Hennion, J. Am. Chem. Soc., 1941, 63, 858.
J. A. Cella, J. A. Kelley, and E. F. Kenehan, J. Org. Chem., 1975, 40, 1860.
B. J. Ganem, J. Org. Chem., 1975, 40, 1998.
T. Miyazawa and T. Endo, J. Mon. Catal., 1985, 82, 357.
A. H. Haines, Methods for the Oxidation of Organic Compounds, Academic Press, New York, 1985.
P. L. Anelli, S. Banfi, F. Montanari, and S. Quici, J. Org. Chem., 1989, 54, 2970.
J. Einborn, C. Einborn, F. Ratajczak, and J. L. Pierre, J. Org. Chem., 1996, 61, 7452.
S. D. Rychnovsky and R. Vaidyanthan, J. Org. Chem., 1999, 64, 310.
G. Charlot, Les methodes de la chimie analytique, Paris, 1961.
Organikum. Organischchemisches Grundpraktikum, Deutscher Verlag der Wissenschaften, Berlin, 1976.
A. P. Borisov, L. A. Petrova, and V. D. Makhaev, Zh. Obshch. Khim., 1992, 62, 15 [Russ. J. Gen. Chem., 1992, 62 (Engl. Transl.)].
I. T. Goronovskii, Yu. P. Nazarenko, and E. F. Nekryach, Kratkii spravochnik po khimii [Concise Handbook of Chemistry], Naukova Dumka, Kiev, 1974, 992 pp. (in Russian).
R. W. Binkley, Synth. Commun., 1976, 6, 281.
H. W. Geluk and J. L. Schlatmann, Tetrahedron, 1968, 24, 5361.
A. Howard, Tetrahedron Lett., 1975, 2257.
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Khusnutdinov, R.I., Schadneva, N.A., Baiguzina, A.R. et al. The Mn(acac)3—RCN—CCl4 system as a new efficient reagent for the oxidation of secondary alcohols into ketones. Russian Chemical Bulletin 51, 1065–1067 (2002). https://doi.org/10.1023/A:1019638407972
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DOI: https://doi.org/10.1023/A:1019638407972