Abstract
A simple, rapid, and efficient oxidation of oximes to the corresponding ketones and aldehydes with manganese dioxide catalyzed by kieselguhr under solvent-free conditions at room temperature in the yields between 82 and 98 is described. It seems that kieselguhr in the present procedure can highly expedite the reaction rate. By comparing to other methods described previously, the main advantages of this oxidation are that the oxidations are more efficient, the reaction conditions are milder, the reaction times are shorter, and the work-up is easier. Furthermore, the amount of manganese dioxide used in this oxidation is largely decreased.
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References
T.W. Green, P. Wuts, Protective groups in organic synthesis, 2nd edn. (Wiley, New York, 1991)
P. Laszlo, E. Polla, Synthesis 439 (1985)
G.W. Kabalka, R.D. Pace, P.P. Wadgaonkaf, Synth. Commun. 20, 2453 (1990)
G.S. Zhang, H. Gong, D.H. Yang, M.F. Chen, Synth. Commun. 29, 1165 (1999)
S.R. Sandler, W. Karo, Organic functional group preparations, 2nd edn, vol 3 (Academic Press, San Diego, 1989)
B.C. Ranu, D.C. Sarkar, J. Org. Chem. 53, 878 (1988)
A. Corsaro, U. Chiacchio, V. Pistara, Synthesis 1903 (2001)
A. Corsaro, M.A. Chiacchio, V. Pistara, Curr. Org. Chem. 13, 482 (2009)
S. Sahu, S. Sahu, S. Patel, S. Dash, B.K. Mishra, Indian J. Chem. 47B, 259 (2008)
A.J. Fatiadi, Synthesis 65(Part 1) and 133(Part 2) (1976)
T. Shinada, K. Yoshihara, Tetrahedron Lett. 36, 6701 (1995)
L. Huang, Q. Wang, Y. Ma, J.D. Lou, C. Zhang, Synth. Commun. 41, 1682 (2011)
J.D. Lou, Synth. Commun. 19, 1841 (1989)
J.D. Lou, W. Lou, Synth. Commun. 27, 3697 (1997)
J.D. Lou, M. Wang, L. Zhu, Z. Fang, Catal. Commun. 4, 647 (2003)
J.D. Lou, X. Chen, M. Wang, Oxid. Commun. 27, 610 (2004)
J.D. Lou, Y. Ma, C. Gao, L. Li, Synth. React. Inorg. Metal. Org. Nano-Metal. Chem. 36, 381 (2006)
J.D. Lou, L. Zhu, Y. Ma, L. Li, Synth. Commun. 36, 3061 (2006)
J.D. Lou, L. Li, N. Vatanian, X. Lu, X. Yu, Synth. React. Inorg. Metal. Org. Nano-Metal. Chem. 38, 373 (2008)
G.Q. Wang, C. Zhang, N. Vatanian, J.D. Lou, Synth. React. Inorg. Metal. Org. Nano-Metal. Chem. 38, 481 (2008)
J.D. Lou, C. Zhang, G. Wang, C. Gao, Synth. React. Inorg. Metal. Org. Nano-Metal. Chem. 39, 6 (2009)
J.D. Lou, J. Ge, X.N. Zou, C. Zhang, Q. Wang, Y.C. Ma, Oxid. Commun. 34, 361 (2011)
J.D. Lou, X. Lu, L. Huang, C. Zhang, Q. Wang, X. Zou, Synth. React. Inorg. Metal. Org. Nano-Metal. Chem. 41, 1278 (2011)
L. Huang, J.D. Lou, Y. Ma, Q. Wang, C. Zhang, Adsorpt. Sci. Technol. 29, 871 (2011)
J.D. Lou, F. Lin, X. Lu, Q. Wang, X. Zou, Synth. React. Inorg. Metal. Org. Nano-Metal. Chem. 42, 282 (2012)
L.F. Fieser, M. Fieser, Reagents for organic synthesis, vol 1 (Wiley, New York, 1967) (subsequent volumes in the series)
A. Mckillop, D.W. Young, Synthesis 401 (Part 1) and 481 (Part 2) (1979)
P. Laszlo, Preparative chemistry using supported reagents (Academic Press, San Diego, 1987)
J.D. Metzger, Angew. Chem. Int. Ed. 37, 2975 (1998)
K. Tanaka, F. Toda, Chem. Rev. 100, 1025 (2000)
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Zheng, W., Huang, C., Zhang, C. et al. A simple, rapid, and efficient oxidation of oximes to ketones and aldehydes with manganese dioxide catalyzed by kieselguhr under solvent-free conditions. Res Chem Intermed 39, 499–504 (2013). https://doi.org/10.1007/s11164-012-0573-2
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DOI: https://doi.org/10.1007/s11164-012-0573-2