Examples:
K. M. Brummond, P. C. Still, H. Chen, Org. Lett. 2004, 6, 149. |
P. C. Mukharji, A. N. Ganguly, Tetrahedron 1969, 25, 5281. |
2.1.4 Mn(VII) Reagents as an Oxidant
Potassium permanganate (KMnO4) is a strong oxidizing agent, and its reactivity depends on whether it is used in acid, neutral or basic conditions. In acid solution, Mn(VII) is reduced to Mn(II), while in basic and neutral conditions, MnO2 is usually formed.
2.1.4.1 Oxidation of Aromatic Side Chains
Alkyl side chain present in aromatic ring is readily oxidized to carboxylic acids (Scheme 15).
Scheme 15 |
Application in the synthesis of Saccharin
2.1.4.2 Oxidation of Aromatic Rings
Benzene ring can be cleaved if it is fused to heterocyclic ring system. Thus, quinonline and isoquinoline can be oxidized to dicarboxylic acids in the presence of alkaline KMnO4 (Scheme 16).
Scheme 16 |