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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.
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.
Neopentyl glycol (IUPAC name: 2,2-dimethylpropane-1,3-diol) is an organic chemical compound. It is used in the synthesis of polyesters , paints , lubricants , and plasticizers . When used in the manufacture of polyesters, it enhances the stability of the product towards heat, light, and water.
Propylene glycol (IUPAC name: propane-1,2-diol) is a viscous, colorless liquid. It is almost odorless and has a faintly sweet taste. Its chemical formula is CH 3 CH(OH)CH 2 OH. As it contains two alcohol groups, it is classified as a diol. An aliphatic diol may also be called a glycol.
The polyol pathway is a two-step process that converts glucose to fructose. [1] In this pathway glucose is reduced to sorbitol, which is subsequently oxidized to fructose. It is also called the sorbitol-aldose reductase pathway. The pathway is implicated in diabetic complications, especially in microvascular damage to the retina, [2] kidney, [3 ...
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
Glyoxal was first prepared and named by the German-British chemist Heinrich Debus (1824–1915) by reacting ethanol with nitric acid. [4] [5]Commercial glyoxal is prepared either by the gas-phase oxidation of ethylene glycol in the presence of a silver or copper catalyst (the Laporte process) or by the liquid-phase oxidation of acetaldehyde with nitric acid.
When cyclopentadiene is used as the diene, the vicinal norbornene diol bicyclo[2.2.1]hept-5-ene-2,3-diol is formed after hydrolysis. The Swern oxidation to the 1,2-ketone bicyclo[2.2.1]hept-5-ene-2,3-dione proceeds (in the variant with trifluoroacetic anhydride instead of oxalyl chloride ) with a yield of 73%.