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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.
The by-products are dimethyl sulfide ((CH 3) 2 S), carbon monoxide (CO), carbon dioxide (CO 2) and—when triethylamine is used as base—triethylammonium chloride (Et 3 NHCl). Of the volatile by-products, dimethyl sulfide has a strong, pervasive odour and carbon monoxide is acutely toxic, so the reaction and the work-up needs to be performed ...
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]
for dimethyl sulfoxide/water [4] P = 550 mm Hg BP Temp. °C % by mole water liquid ... for dimethyl sulfoxide/ethanol [4] P = 14.665 kPa BP Temp. °C % by mole DMSO ...
The following figure shows the reaction mechanism: [2] Reaktionsmechanismus Albright-Goldman-Oxidation. 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 ...
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 .
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.