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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.
DMSO reductase is a molybdenum-containing enzyme that catalyzes reduction of dimethyl sulfoxide (DMSO) to dimethyl sulfide (DMS). This enzyme serves as the terminal reductase under anaerobic conditions in some bacteria, with DMSO being the terminal electron acceptor. During the course of the reaction, the oxygen atom in DMSO is transferred to ...
The Albright–Goldman oxidation is a name reaction of organic chemistry, first described by the American chemists J. Donald Albright and Leon Goldman in 1965. [1] The reaction is particularly suitable for the synthesis of aldehydes from primary alcohols. Analogously, secondary alcohols can be oxidized to form ketones.
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]
It can be oxidized to dimethyl disulfide: 2CH 3 SH + [O] → CH 3 SSCH 3 + H 2 O. Further oxidation takes the disulfide to two molecules of methanesulfonic acid, which is odorless. Bleach deodorizes methanethiol in this way.
Any non-tertiary benzylic alkyl group will be oxidized to a carboxyl group by aqueous potassium permanganate (KMnO 4) or concentrated nitric acid (HNO 3): (ArCHR 2 → ArCOOH). [6] Finally, the complex of chromium trioxide and 3,5-dimethylpyrazole (CrO 3 −dmpyz) will selectively oxidize a benzylic methylene group to a carbonyl: (ArCH 2 R → ...
However, a significant portion of DMS in seawater is oxidized to dimethyl sulfoxide (DMSO). Relevant to global climate, DMS is thought to play a role in the Earth's heat budget by decreasing the amount of solar radiation that reaches the Earth's surface. This occurs through degradation of DMS in the atmosphere into hygroscopic compounds that ...
The by-products are dimethyl sulfide (Me 2 S), carbon monoxide (CO), carbon dioxide (CO 2) and – when triethylamine is used as base – triethylammonium chloride (C 6 H 15 NHCl). The related N-tert-Butylbenzenesulfinimidoyl chloride combines both the sulfur(IV), the base, and the activating Lewis acid in one molecule.