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Although the classic substrate for the Criegee oxidation are 1,2-diols, the oxidation can be employed with β-amino alcohols, [10] α-hydroxy carbonyls, [11] and α-keto acids, [12] In the case of β-amino alcohols, a free radical mechanism is proposed. The Criegee oxidation can also be employed with 2,3-epoxy alcohols forms α-acetoxy carbonyls.
In a vicinal diol, the two hydroxyl groups occupy vicinal positions, that is, they are attached to adjacent atoms. These compounds are called glycols [5] (though the term can be used more widely). Examples include ethane-1,2-diol or ethylene glycol HO−(CH 2) 2 −OH, a common ingredient of antifreeze products.
[1,3] diols have a tendency to eliminate water following the monooxidation by Fétizon's reagent to form an enone. [8] Upon oxidation with Fetizon's reagent, a 1,3 diol may eliminate water to produce an enone. Under differing structural conditions, [1,2] diols can form diketones in the presence of Fétizon's reagent.
benzene-1,2-diol benzene-1,3-diol benzene-1,4-diol Other names ... The Dakin oxidation is an organic redox reaction in which an ortho- or para-hydroxylated ...
Glycol cleavage is a specific type of organic chemistry oxidation. The carbon–carbon bond in a vicinal diol (glycol) is cleaved and instead the two oxygen atoms become double-bonded to their respective carbon atoms. Depending on the substitution pattern in the diol, these carbonyls will be ketones and/or aldehydes. [1]
The oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate (gem-diol, R-CH(OH) 2) by reaction with water. Thus, the oxidation of a primary alcohol at the aldehyde level without further oxidation to the carboxylic acid is possible by performing the reaction ...
Dihydroxylation is the process by which an alkene is converted into a vicinal diol. Although there are many routes to accomplish this oxidation, the most common and direct processes use a high-oxidation-state transition metal (typically osmium or manganese). The metal is often used as a catalyst, with some other stoichiometric oxidant present. [1]
The pinacol–pinacolone rearrangement is a method for converting a 1,2-diol to a carbonyl compound in organic chemistry. The 1,2-rearrangement takes place under acidic conditions. The name of the rearrangement reaction comes from the rearrangement of pinacol to pinacolone. [1]