SODIUM PERMANGANATE 1
Sodium Permanganate 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 exam-
NaMnO4·H2O
ples of this oxidation are shown in eqs 1 4.
[10101-50-5] H2MnNaO5 (MW 159.95) OH O
(1)
InChI = 1/Mn.Na.H2O.4O/h;;1H2;;;;/q;+1;;;;;-1/rMnO4.Na.H2O/
95%
Hex Hex
c2-1(3,4)5;;/h;;1H2/q-1;+1;
InChIKey = DJKJCISMVZLEDS-YMGRVYDCAJ
O
Hex
(2)
OH
Hex
(oxidant; capable of converting secondary alcohols into ketones, 67%
OH
primary alcohols and aldehydes into carboxylic acids, sulfides into
sulfones, and amines into the corresponding nitro compounds;
OH O
less effective oxidant for unsaturated alcohols; unreactive toward
alkanes, alkenes, alkynes, and epoxides)
(3)
47%
Physical Data: solid; decomposes with evolution of oxygen at
ć%
170 C; d 2.46 g cm-3.
Solubility: sol water; insol hexane.
OH O
Form Supplied in: purple solid; commercially available.
(4)
11%
C5H11 C5H11
Handling, Storage, and Precautions: oxidant; store in glass
vessel at rt.
Oxidation of Sulfides. Dialkyl sulfides are converted to the
corresponding sulfones under similar conditions (eq 5).1
Introduction. When dissolved in water, the chemical properi-
(5)
ties of sodium permanganate are very similar to those of Potassium
Bu2SBu2SO2
91%
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. 1. Menger, F. M.; Lee, C., Tetrahedron Lett. 1981, 22, 1655.
Oxidation of Alcohols. When 3 mmol of an alcohol in 15 mL
Donald G. Lee
of hexane is stirred with 1.92 g (12 mmol) of NaMnO4·H2Oat
University of Regina, Regina, Saskatchewan, Canada
Avoid Skin Contact with All Reagents