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[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.
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 ...
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.
Primary alcohols (R−CH 2 OH) can be oxidized either to aldehydes (R−CHO) or to carboxylic acids (R−CO 2 H). The oxidation of secondary alcohols (R 1 R 2 CH−OH) normally terminates at the ketone (R 1 R 2 C=O) stage. Tertiary alcohols (R 1 R 2 R 3 C−OH) are resistant to oxidation.
In organic chemistry, the Malaprade reaction or Malaprade oxidation is a glycol cleavage reaction in which a vicinal diol is oxidized by periodic acid or a periodate salt to give the corresponding carbonyl functional groups. [1] [2] The reaction was first reported by Léon Malaprade in 1928. [3] [4] Amino alcohols are also cleaved. [5]
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]
benzene-1,2-diol benzene-1,3-diol benzene-1,4-diol ... Structure All three of these ... The Dakin oxidation is an organic redox reaction in which an ortho- or para ...