Abstract
A facile and efficient procedure for the oxidative cleavage of oximes to their parent aldehydes and ketones by grinding with potassium permanganate-graphite at room temperature under solvent-free conditions in the yields between 80 and 94% is described. All reactions are complete in 5 min.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Wuts, P.G.M. and Greene, T.W., Greene’s Protective Groups In Organic Synthesis, 4th Edition, Wiley, New York, 2006.
Solomons, T.W.G., Fryhle, C.B., and Snyder, S.A., Organic Chemistry, New York: John Wiley & Sons, 2014.
Sandle, S.R. and Karo, R.W., Organic Functional Group Preparations, San Diego: Academic Press, 1989.
Smith, M.B., March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, New York: John Wiley & Sons, 2013.
Sandler, S.R. and Karo, W., Organic Functional Group Preparations, vol. 3, 2nd Ed., San Diego: Academic Press, 1989.
Haines, H., Methods for The Oxidation of Organic Compounds, Alcohols, Alcohol Derivatives, Alkyl Halides, Nitroalkanes, Alkyl Azides, Carbonyl Compounds, Hydroxyarenes And Aminoarenes, Academic Press: London, 1988
Sahu, S., Sahu, S., Patel, S., Dash, S., and Mishra, B.K., Indian J. Chem., 2008, vol. 47B, p.259.
Shaabani, A., Naderi, S., Rahmati, A., Badri, Z., Darvishi, M., and Lee, D.G., Synthesis, 2005, p. 3023.
Hajipour, A.R. and Ruoho, A.E., J. Iranian Chem. Soc., 2004, vol. 1, p.159.
Mohammadpoor-baltork, I., Khodaei, M.M., Hajipour, A.R., and Aslani, E.A., Monatsh Chem., 2003, vol. 134, p.539.
Imanzadeh, G.H., Hajipour, A.R., and Mallakpour, S.E., Synth. Commun., 2003, vol. 33, p.735.
Chrisman, W., Blankinship, M.J., Taylor, B., and Harris, C.E., Tetrahedron Lett., 2001, vol. 42, p. 4775.
Jadhav, V.K., Wadgaonkar, P.P., Joshi, P.L., and Salunkhe, M.M., Synth. Commun., 1999, vol. 29, p. 1989.
Zhou, Y.F., Lin, F., Lu, X.L., Zhang, C., Wang, Q., Zou, X., and Lou, J.D., Oxid. Commun., 2012, vol. 35, p.72.
Zhu, L., Huang, C., Shi, C., Lin, F., Zhang, C., and Lou, J.D., Oxid Commun., 2012, vol. 35, p.389.
Lou, J.D., Lin, F., Huang, L., and Zou, L.X., Synth. React. Inorg. Me, 2012, vol. 42, p. 1027.
Zhu, L., Lou, Z., Lin, J., Zheng, W., Zhang, C., Lou, J.D., Res. Chem. Intermediat., 2013, vol. 39, no. 9, pp. 4315–4320.
Zhu, L., Huang, C., Shi, C., Lin, F., Zhang, C., and Lou, J.D., Oxid. Commun., 2012, vol. 35, no. 2, p.394.
Lou, J.D., Lin, F., Zhang, C., Zhu, L.Y., and Lin, J., Oxid. Commun., 2013, vol. 36, no. 2, pp. 492–496.
Fatiadi, A.J., Synthesis, 1987, pp. 85–127.
Fieser, L.F. and Fieser, M., Reagents for Organic Synthesis, New York: Wiley-Intersci., 1972.
Mckillop, D.W., Synthesis, 1979, pt. 1, pp. 401–422; pt. 2, pp. 481–500.
Laszlo, P., Preparative Chemistry Using Supported Reagents, San Diego, CA: Academic Press, 1987.
Smith, K., Solid Supports and Catalysts in Organic Synthesis, New York: Prentice Hall, 1992.
Metzger, J.D., Angew Chem. Int. Ed., 1998, vol. 37, p. 2975.
Tanaka, K. and Toda, F., Chem. Rev., 2000, vol. 100, p. 1025.
Sineriz, F., Thomassigny, C., and Lou, J.D., Curr. Org. Synth., 2004, vol. 1, p. 137.
Author information
Authors and Affiliations
Corresponding authors
Additional information
The text was submitted by the authors in English.
Rights and permissions
About this article
Cite this article
Zhu, LY., Song, Lz., Chen, W. et al. Regeneration of aldehydes and ketones by the oxidation of oximes using potassium permanganate-graphite with grinding under solvent-free conditions. Russ J Appl Chem 90, 1326–1329 (2017). https://doi.org/10.1134/S1070427217080225
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070427217080225