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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 4
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Original Articles

Potassium Permanganate Oxidation of Organic Compounds

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Pages 571-580 | Received 25 Aug 2004, Published online: 12 Apr 2011
 

Abstract

It has been discovered that potassium permanganate is an effective heterogeneous oxidant, even without resorting to the use of a solid support, if acetonitrile is employed as the solvent. Primary benzylic and secondary alcohols are converted to the corresponding aldehydes and ketones, alkyl arenes are oxidized to the corresponding α‐ketones in good yields using this procedure, and both alkyl and aryl sulfides are smoothly converted to the corresponding sulfones, also in excellent yields. When methylene chloride is used as the solvent, instead of acetonitile, the yields of aldehydes, ketones, α‐ketones, and sulfones are reduced. However, the oxidation of thiols to disulfides proceeds satisfactorily when methylene chloride is the solvent.

Acknowledgment

Financial support on the Research Council of Shahid Beheshti University is acknowledged.

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