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Methanesulfonyl chloride is mainly used to give methanesulfonates by its reaction with alcohols in the presence of a non-nucleophilic base. [8] In contrast to the formation of toluenesulfonates from alcohols and p-toluenesulfonyl chloride in the presence of pyridine, the formation of methanesulfonates is believed to proceed via a mechanism wherein methanesulfonyl chloride first undergoes an ...
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 ...
Methanesulfonic acid (MsOH, MSA) or methanesulphonic acid (in British English) is an organosulfuric, colorless liquid with the molecular formula CH 3 SO 3 H and structure H 3 C−S(=O) 2 −OH. It is the simplest of the alkylsulfonic acids ( R−S(=O) 2 −OH ).
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.
If produced from oleochemical feedstock or the Ziegler process, the hydrocarbon chain of the alcohol will be linear. If derived using the oxo process, a low level of branching will appear usually with a methyl or ethyl group at the C-2 position, containing even and odd amounts of alkyl chains. [3] These alcohols react with chlorosulfuric acid:
The intermediate benzenesulfonic acid can be chlorinated with thionyl chloride as well. Benzenesulfonyl chloride, the most important sulfonyl halide, can also be produced by treating sodium benzenesulfonate with phosphorus pentachlorides. [5] Benzenediazonium chloride reacts with sulfur dioxide and copper(I) chloride to give the sulfonyl chloride:
The general formula is R−SO 2 NR'R" or R−S(=O) 2 −NR'R", where each R is some organic group; for example, "methanesulfonamide" (where R = methane, R' = R" = hydrogen) is CH 3 SO 2 NH 2. Any sulfonamide can be considered as derived from a sulfonic acid by replacing a hydroxyl group ( −OH ) with an amine group.
The addition of at least 2 equivalents of base — typically triethylamine — will deprotonate the alkoxysulfonium ion to give the sulfur ylide 7. In a five-membered ring transition state, the sulfur ylide 7 decomposes to give dimethyl sulfide and the desired carbonyl compound 8. The mechanism of the Swern oxidation.