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DOI: 10.1055/sos-SD-027-00002

Aggarwal, V.; Richardson, J.Science of Synthesis, (20042743.

Sulfoxonium salts 55 are readily deprotonated to give the corresponding sulfoxonium ylides 56 (Scheme 28). The applicability of this method is limited by the number of sulfoxonium salts that can be prepared, as alkylation of sulfoxides generally gives both S- and O-alkylation products. In only a few exceptional cases, most notably for the reaction of dimethyl sulfoxide with iodomethane, does S-alkylation occur exclusively.[‌128‌] This method provides a simple synthesis of trimethylsulfoxonium iodide (53, X=I), and thereby the ylide dimethylsulfoxonium methylide (52). More substituted sulfoxonium ylides are prepared by hydrogen atom substitution of 52 (see Section, thereby making it the most popular and important of all sulfoxonium ylides.

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