Sodium Permanganate

NaMnO4.H2O

[10101-50-5]  · H2MnNaO5  · Sodium Permanganate  · (MW 159.95)

(oxidant; capable of converting secondary alcohols into ketones, primary alcohols and aldehydes into carboxylic acids, sulfides into sulfones, and amines into the corresponding nitro compounds; less effective oxidant for unsaturated alcohols; unreactive toward alkanes, alkenes, alkynes, and epoxides)

Physical Data: solid; decomposes with evolution of oxygen at 170 °C; d 2.46 g cm-3.

Solubility: sol water; insol hexane.

Form Supplied in: purple solid; commercially available.

Handling, Storage, and Precautions: oxidant; store in glass vessel at rt.

Introduction.

When dissolved in water, the chemical properities of sodium permanganate are very similar to those of Potassium Permanganate; when used heterogeneously, it is a slightly less reactive oxidant than Copper(II) Permanganate heptahydrate. In common with Cu(MnO4)2, anhydrous sodium permanganate is not a good heterogeneous oxidant.

Oxidation of Alcohols.

When 3 mmol of an alcohol in 15 mL of hexane is stirred with 1.92 g (12 mmol) of NaMnO4.H2O at reflux for 2.5 h, the resulting ketone or carboxylic acid can be easily isolated by filtering the mixture and flash evaporating the solvent.1 The yields for allylic alcohols are lower. Typical examples of this oxidation are shown in eqs 1-4.

Oxidation of Sulfides.

Dialkyl sulfides are converted to the corresponding sulfones under similar conditions (eq 5).1


1. Menger, F. M.; Lee, C. TL 1981, 22, 1655.

Donald G. Lee

University of Regina, Saskatchewan, Canada



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