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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.
Hydrogen peroxide is a typical oxidant—for example, with dimethyl sulfide (S(CH 3) 2): [9] S(CH 3) 2 + H 2 O 2 → OS(CH 3) 2 + H 2 O OS(CH 3) 2 + H 2 O 2 → O 2 S(CH 3) 2 + H 2 O. In analogy to their easy alkylation, sulfides bind to metals to form thioether complexes. Consequently, Lewis acids do not decompose thioethers as they do ethers ...
In organic chemistry, a sulfone is a organosulfur compound containing a sulfonyl (R−S(=O) 2 −R’) functional group attached to two carbon atoms. The central hexavalent sulfur atom is double-bonded to each of two oxygen atoms and has a single bond to each of two carbon atoms, usually in two separate hydrocarbon substituents .
With respect to donor properties, dimethyl sulfide is a soft ligand with donor properties weaker than phosphine ligands. [3] Such complexes are generally prepared by treating the metal halide with the thioether. Chloro(dimethyl sulfide)gold(I) can however be prepared by redox reaction of elemental gold and DMSO in the presence of hydrochloric ...
The bond dissociation energies for dimethyl sulfide and dimethyl ether are respectively 73 and 77 kcal/mol (305 and 322 kJ/mol). Sulfides are typically prepared by alkylation of thiols. Alkylating agents include not only alkyl halides, but also epoxides, aziridines, and Michael acceptors. [6] They can also be prepared via the Pummerer ...
Diethyl sulfide is a Lewis base, classified as a soft ligand (see also ECW model).Its relative donor strength toward a series of acids, versus other Lewis bases, can be illustrated by C-B plots.
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 ...
Sulfonium compounds are usually synthesized by the reaction of thioethers with alkyl halides. For example, the reaction of dimethyl sulfide with iodomethane yields trimethylsulfonium iodide: CH 3 –S–CH 3 + CH 3 –I → (CH 3) 3 S + I −. The reaction proceeds by a nucleophilic substitution mechanism (S N 2) where iodide is the leaving group.