Synthesis
Sulfonium compounds are usually be synthesized from the reaction of thioethers with alkyl halides. For example, the reaction of dimethyl sulfide with iodomethane yields trimethylsulfonium iodide:
- CH3–S–CH3 + CH3–I → (CH3)3S+ + I−
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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