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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.
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.
For example, dimethyl sulfide is oxidized to dimethyl sulfoxide and then further to dimethyl sulfone. Unsymmetrical sulfides are prochiral, thus their oxidation gives chiral sulfoxides. This process can be performed enantioselectively. [9] [10] Symmetrical sulfoxides can be formed from a diorganylzinc compound and liquid sulfur dioxide. [11]
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
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.
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.
Rather, it is formed by oxidation of dimethyl sulfide with an oxidant (NCS). The reaction mechanism of Corey–Kim oxidation Under Corey–Kim conditions allylic and benzylic alcohols have a tendency to evolve to the corresponding allyl and benzyl chlorides unless the alcohol activation is very quickly followed by addition of triethylamine .