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Name Reactions


Jacobsen Epoxidation


Recent Literature


An effective epoxidation of lipophilic alkenes using hydrogen peroxide was accomplished with a manganese sulfate/bicarbonate catalytic system in an ionic liquid at room temperature.
K.-H. Tong, K.-Y. Wong, T. H. Chan, Org. Lett., 2003, 5, 3423-3425.


An epoxidation of alkenes using hydrogen peroxide as the terminal oxidant is promoted by catalytic amounts (1.0-0.1 mol %) of manganese(2+) salts, and must be performed using at least catalytic amounts of bicarbonate buffer. Various aryl-substituted, cyclic, and trialkyl-substituted alkenes were epoxidized under these conditions using 10 equiv of hydrogen peroxide, but monoalkyl-alkenes were not. Additives such as sodium acetate and salicylic acid enhanced the rate of the desired epoxidation reaction by 2-3 times. Possible mechanisms for the reaction are discussed.
B. S. Lane, M. Vogt, V. J. DeRosa, K. Burgess, J. Am. Chem. Soc., 2002, 124, 11946-11954.


Readily available Mn(III) complexes catalyze alkene epoxidation by bleach in good yields. A highly enantioselective epoxidation catalyst was developed through a logical sequence of ligand modifications.
E. N. Jacobsen, W. Zhang, A. R. Muci, J. R. Ecker, L. Deng, J. Am. Chem. Soc., 1991, 113, 7063-7064.


The complex [MnII(R,R-mcp)(CF3SO3)2] is a very efficient and practical catalyst for the epoxidation of a wide scope of olefins including terminal, tertiary, cis and trans internal, enones, and methacrylates using peracetic acid as the terminal oxidant.
A. Murphy, G. Dubois, T. D. P. Stack, J. Am. Chem. Soc., 2003, 125, 5250-5251.


Reactions of vinyl azides with monocyclic cyclopropanols provided pyridines in the presence of Mn(acac)3, whereas those with bicyclic cyclopropanols led to the formation of 2-azabicyclo[3.3.1]non-2-en-1-ol derivatives using a catalytic amount of Mn(acac)3.
Y.-F. Wang, S. Chiba, J. Am. Chem. Soc., 2009, 131, 12570-12572.


Mn(OAc)3 based regioselective oxidation of various 2-cyclopentenone, 2-cyclohexenone and aromatic ketone derivatives in benzene afforded the corresponding tertiary α'-acetoxy oxidation products in good yields.
C. Tanyeli, C. Iyiguen, Tetrahedron, 2003, 59, 7135-7139.