Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Trimethylsulfoxonium iodide is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride.[1] The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides.
This compound is commercially available. It may be prepared by the reaction of dimethyl sulfoxide and iodomethane:[2]
(CH3)2SO + CH3I → (CH3)3SO+I−
^Corey, E. J.; Chaykovsky, Michael. "Methylenecyclohexane Oxide". Organic Syntheses; Collected Volumes, vol. 5, p. 755.
^Lampman, Gary M.; Koops, Roger W.; Olden, Caroline C. (1985). "Phosphorus and sulfur ylide formation: Preparation of 1-benzoyl-2-phenylcyclopropane and 1,4-diphenyl-1,3-butadiene by phase transfer catalysis". J. Chem. Educ.62 (3): 267. Bibcode:1985JChEd..62..267L. doi:10.1021/ed062p267.
and 7 Related for: Trimethylsulfoxonium iodide information
Trimethylsulfoxoniumiodide is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride. The latter compound...
dimethyl sulfoxide with methyl iodide can yield trimethylsulfoxoniumiodide. Treated with sodium hydride, trimethylsulfoxonium forms dimethylsulfoxonium methylide...
bonds, using acid or base catalysis. Trimethylsulfoxoniumiodide, made from dimethyl sulfoxide and methyl iodide can be recrystallized from deuterium...
nucleophilic toward hard electrophiles. With methyl iodide it forms trimethylsulfoxoniumiodide, [(CH3)3SO]I: (CH3)2SO + CH3I → [(CH3)3SO]I This salt...
amide with 4-fluorobenzylamine, followed by methylation using trimethylsulfoxoniumiodide. Use of that reagent ensures the required chemoselectivity so...
trimethylsulfonium iodide: (CH3)2S + CH3I → [(CH3)3S]+I− An extra oxygen atom can bond to the sulfur atom to yield the trimethylsulfoxonium ion [(CH3)3S=O]+...
Johnson–Corey–Chaykovsky reaction by reaction of canrenone with trimethylsulfoxoniumiodide and sodium hydride. Canrenone Mexrenone Prorenoate potassium...
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