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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 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 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]
Dichlorotetrakis(dimethyl sulfoxide) ruthenium(II) describes coordination compounds with the formula RuCl 2 (dmso) 4, where DMSO is dimethylsulfoxide. Both cis and trans isomers are known, but the cis isomer is more common. The cis isomer is a yellow, air-stable solid that is soluble in some organic solvents.
The reaction requires one equivalent each of the diimide, which is the dehydrating agent, and the sulfoxide, the oxidant: (CH 3) 2 SO + (CyN) 2 C + R 2 CHOH → (CH 3) 2 S + (CyNH) 2 CO + R 2 C=O. Typically the sulfoxide and diimide are used in excess. [3] The reaction cogenerates dimethyl sulfide and a urea.
Dimethyl sulfide has a characteristic odor commonly described as cabbage-like.It becomes highly disagreeable at even quite low concentrations. Some reports claim that DMS has a low olfactory threshold that varies from 0.02 to 0.1 ppm [clarification needed] between different persons, but it has been suggested that the odor attributed to dimethyl sulfide may in fact be due to disulfides ...
Being weakly basic, sulfoxide ligands are generally labile, i.e. they are rapidly displaced by other more basic ligands. O-bonded sulfoxide ligands are susceptible to oxidation at sulfur. In this way, the weakly bonded ligand is converted into a leaving group, such as dimethylsulfone. Since dmso is susceptible to deprotonation by strong base ...