Chemistry Reference
In-Depth Information
TABLE 6.3. Typical Reactions of Permanganate
Reductant
Process
Product
RCH=CHR
cis
-Dihydroxylation
OHOH
| |
RCH
-
CHR
RCH=CHR
Oxidative cleavage
O O
|| ||
RCH or RCOH
RCH=CR
2
Ketol formation
O
|| |
RC-CR
2
OH
R
2
C=CR
2
Oxidative cleavage
R
2
C=O
ArCH
3
Oxidation
ArCOOH
ARCH
2
R
Oxidation
O
||
ArCR
RSH
Oxidation
ArSO
3
H
ArSH
Oxidation
RSSR
R
2
CHNH
2
Oxidation
R
2
C=O
ArNH
2
Oxidative coupling
ArN=Nar
Adapted from Singh and Lee [215] with the permission of the American Chemical Society.
Advances have also been made to identify the oxidation states of Mn
formed in
in situ
chemical oxidation of the organic compound by KMnO
4
and
in solid surfaces of filtration media samples from drinking water treatment
[226, 227].
The reactivity of the permanganate ion with several inorganic and organic
compounds has been reviewed [215, 216, 221, 228-230]. The results of the
oxidation kinetics and mechanism indicate the possibility of several mecha-
nisms, depending on the nature of the substrate, the reaction conditions, and
the nature of the reactive species of manganese [221]. Recent oxidation pro-
cedures include the use of solid KMnO
4
adsorbed onto a solid support as a
heterogeneous reagent or under solvent-free conditions [215]. The oxidation
of alkanes and arylalkanes by the
MnO
−
ion may be accelerated with the use
of an acetonitrile-BF
3
reaction mixture [231, 232]. Density functional theory
(DFT) has been utilized in an effort to understand the reaction mechanisms
[231, 233]. Below is a summary of the reactivity of permanganate with amino
acids and amino polycarboxylates.
6.2.3.1 Amino Acids.
The oxidation of amino acids by permanganate in
acidic and neutral media has been extensively studied [234-236, 236-244]. The
oxidation of amino acids resulted in aldehydes, ammonia, and CO
2
as products
of the reactions (e.g., Eqs. 6.68-6.70) [234, 239]:
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