2.1.4.3 Oxidation of Alcohols
Alkaline KMnO₄ and barium permanganate selectively oxidize alcohols to aldehydes and ketones (Scheme 17).

Scheme 17

2.1.4.4 Oxidation of Aldehydes

Aldehydes are oxidized to carboxylic acids with good yield at ambient temperature (Scheme 18).

Scheme 18

2.1.4.5 1,2-Dihydroxylation

The alkaline KMnO₄ is most commonly used for selective cis-dihydroxylation from the less hindered side of the double bond (Scheme 19).

Scheme 19

The permanganate ion adds to the double bond to form a cyclic ester, which after alkaline hydrolysis gives the desired cis-1,2-diol (Scheme 20).

Scheme 20

 

Lemieux-von Rudloff Reagent Mixtures of sodium periodate (NaIO4) and potassium permanganate (KMnO4) in aqueous organic solvent used for oxidative cleavage of a double bond.