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In these oxidations, care is required to avoid over oxidation to form the sulfone. 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]
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.
Sulfone is a relatively inert functional group, typically less oxidizing and 4 bel more acidic than sulfoxides. In the Ramberg–Bäcklund reaction and the Julia olefination, sulfones are converted to alkenes by the elimination of sulfur dioxide. [13] However, sulfones are unstable to bases, eliminating to give an alkene. [14]
Dimethyl sulfide is considered the most important thioether produced industrially. One major use is for the production of borane dimethyl sulfide from diborane: [19] B 2 H 6 + 2 (CH 3) 2 S → 2 BH 3 ·S(CH 3) 2. Oxidation of dimethyl sulfide gives the solvent dimethyl sulfoxide. Further oxidation affords dimethyl sulfone.
Dimethyl sulfone (DMSO 2) is an organosulfur compound with the formula (CH 3) 2 SO 2. It is also known by several other names including methyl sulfone and (especially in alternative medicine) methylsulfonylmethane (MSM). [4] This colorless solid features the sulfonyl functional group and is the simplest of the sulfones. It is relatively inert ...
O-bonded sulfoxide ligands are far more common, especially for 1st row metals. S-bonded sulfoxides are only found for soft metal centers, such as Ru(II). Complexes with both O- and S-bonded sulfoxide ligands are known. [4] In some cases, sulfoxides are bridging ligands, with S bonded to one metal and O bonded to the other.
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.
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. [1] They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin.