The reaction of 1,2-diols (vicinal diols) with periodic acid (HIO4) is known as Malaprade oxidation. It involves the oxidative cleavage of the carbon-carbon bond between the two carbons bearing the hydroxyl groups.
- Reaction Principle: The reagent HIO4 cleaves the C-C bond. Each carbon attached to an -OH group is oxidized. A primary alcohol group (−CH2OH) is oxidized to an aldehyde (Formaldehyde, HCHO), and a secondary alcohol group (−CHROH) is oxidized to a higher aldehyde (RCHO).
- Application to Ethylene Glycol: The reactant is HO−CH2−CH2−OH. Cleavage of the central C-C bond converts each −CH2OH group into Formaldehyde.
Reaction: CH2OH−CH2OH+HIO4→2HCHO+HIO3+H2O.