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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 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−).
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.
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.
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.
cis-RuCl 2 (dmso) 4, a representative metal complex of a sulfoxide. Three DMSO ligands are S-bonded to Ru, one is O-bonded. Sulfoxides, especially DMSO, form coordination complexes with transition metals. Depending on the hard-soft properties of the metal, the sulfoxide binds through either the sulfur or the oxygen atom. The latter is ...
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 ...
Dimethyl sulfide (Me 2 S) is treated with N-chlorosuccinimide (NCS), resulting in formation of an "active DMSO" species that is used for the activation of the alcohol. . Addition of triethylamine to the activated alcohol leads to its oxidation to aldehyde or ketone and generation of dimethyl
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