Dess-Martin oxidation
Abstract
Dess-Martin oxidation is a reaction in which an alcohol is oxidized to an aldehyde (or ketone for secondary alcohol). One of the main advantages of this reaction is its mild and selective nature: the oxidation can be carefully controlled, preventing further oxidation of primary alcohols to carboxylic acid.
Keywords
Alcohol, Periodinane, Aldehyde, Ketone
Category
Alcohol
Mechanism
First, the alcohol’s oxygen atom attacks the iodine center of the Dess-Martin periodinane (DMP), leading to the departure of an acetate ion and generating a positively charged intermediate. The acetate ion deprotonates one hydrogen promoting the formation of an alkoxyperiodinane. Simultaneously, collapse of the I-O bond and the release of another acetate ion, deprotonates one α-hydrogen from the original alcohol. This step leads to the aldehyde with a derivative form of the DMP.
