Glycol Cleavage - Reagents

Reagents

Periodic acid (HIO4) and lead tetraacetate (Pb(OAc)4) are the most common reagents used for glycol cleavage. These reactions involve cyclic intermediates which then decompose to form ketones (if the R groups are not H) or aldehydes (if one of the R groups is H).


Warm concentrated potassium permanganate (KMnO4) will react with an alkene to form a glycol and will then immediately cleave the glycol to give stable ketones or oxidizable aldehydes. The aldehydes will react further to become carboxylic acids. Controlling the temperature and concentration of the reagent can keep the reaction from continuing past the formation of the glycol.


Glycol cleavage by periodic acid is called Malaprade periodic acid oxidation first reported by Léon Malaprade in 1934 and also works with alpha aminoalcohols

Read more about this topic:  Glycol Cleavage

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