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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.
Propane-2,2-diol, an example of a geminal diol. A geminal diol has two hydroxyl groups bonded to the same atom. These species arise by hydration of the carbonyl compounds. The hydration is usually unfavorable, but a notable exception is formaldehyde which, in water, exists in equilibrium with methanediol H 2 C(OH) 2
[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 equilibrium in water solution may be shifted towards either compound. For example, the equilibrium constant for the conversion of acetone (H 3 C) 2 C =O to propane-2,2-diol (H 3 C) 2 C(OH) 2 is about 10 −3, [1] while that of formaldehyde H 2 C =O to methanediol H 2 C(OH) 2 is 10 3. [2] For conversion of hexafluoroacetone (F 3 C) 2 C =O to ...
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 ...
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 ...
Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C 6 H 4 (OH) 2. It has two hydroxyl groups bonded to a benzene ring in a para position. It is a white granular solid. Substituted derivatives of this parent compound are also ...
Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol [7]) with the formula (CH 2 OH) 2. It is mainly used for two purposes: as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, flammable, viscous liquid.