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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.
vapor pressure at 20 °C = 0.556 mbar = 0.417 mmHg [2] log 10 of dimethyl sulfoxide vapor pressure. Uses formula ...
The sulfonium oxidations can be categorized into two groups: The methods discovered earliest rely on activated alcohols like alkyl tosylates (Kornblum oxidation) [2] or alkyl chloroformates (from reaction of alcohols with phosgene: Barton-Kornblum) [3] that react as electrophiles when treated with DMSO, liberating an oxygenated leaving group (e.g. OTs−).
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.
All such derivatives feature O-bonded sulfoxides. The tricationic complex in [Rh(dmso) 6](O 3 SCF 3) 3 features one S-bonded and five O-bonded sulfoxide ligands. [10] The complex [Cu(Ph 2 SO) 4] 2+ is square planar, in contrast to the derivative with dmso ligands. The square planar d 8 complex [Rh(dmso) 4] + features a pairs of S- and O-bonded ...
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 ...
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 ...