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The Parikh–Doering oxidation is an oxidation reaction that transforms primary and secondary alcohols into aldehydes and ketones, respectively. [1] The procedure uses dimethyl sulfoxide (DMSO) as the oxidant and the solvent, activated by the sulfur trioxide pyridine complex (SO 3 •C 5 H 5 N) in the presence of triethylamine or diisopropylethylamine as base.
In organic chemistry, the Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol (−OH) is oxidized to an aldehyde (−CH=O) or ketone (>C=O) using oxalyl chloride, dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine.
Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (CH 3) 2 S O.This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water.
First, dimethyl sulfoxide (1) reacts with acetic anhydride to form a sulfonium ion. It reacts with the primary alcohol in an addition reaction. Furthermore, acetic acid is cleaved, so that intermediate 2 is formed. The latter reacts upon elimination of acetic acid and dimethyl sulphide to the aldehyde.
Depicted below is the activated sulfoxide generated during Swern oxidation 4 reacting with a secondary alcohol 5 to form alkoxysulfonium species 6. The mechanism of the Swern oxidation. These activated sulfoxides react as electrophiles when treated with an alcohol, expelling a leaving group that might simultaneously function as counter-ion to ...
Deuterated DMSO, also known as dimethyl sulfoxide-d 6, is an isotopologue of dimethyl sulfoxide (DMSO, (CH 3) 2 S=O)) with chemical formula ((CD 3) 2 S=O) in which the hydrogen atoms ("H") are replaced with their isotope deuterium ("D"). Deuterated DMSO is a common solvent used in NMR spectroscopy.
The most common sulfoxide ligand is dimethyl sulfoxide (dmso). Many sulfoxides are known because an enormous range of organic substituents are possible. When the two substituents differ, the ligand is chiral. Chiral sulfoxides are configurationally stable. One example is methyl phenyl sulfoxide.
Phase behavior Triple point: 291.67 K (18.52 °C), ? Pa Critical point [2]: 720 K (447 °C), 5630 kPa Std enthalpy change of fusion, Δ fus H o: 14.37 kJ/mol Std entropy change