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Sulfonium
A sulfonium ion, also known as sulphonium ion or sulfanium ion, is a positively charged ion (a "cation") featuring three organic substituents attached to sulfur. These organosulfur compounds have the formula ()+. Together with a negatively charged counterion, they give sulfonium salts. They are typically colorless solids that are soluble in organic solvent. ==Synthesis== 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: : + → + Before the above reaction, the sulfur atom has two lone electron pairs. One of these lone pairs links to the methyl group. At the same time, as part of a concerted nucleophilic substitution mechanism (SN2), the iodide leaving group departs. This leaves a positively charged trimethylsulfonium ion, whose charge is balanced by the iodide. The rate of reaction is even faster with stronger methylating agents, such as methyl trifluoromethanesulfonate.
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