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.
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| Names | |
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| Preferred IUPAC name
Trimethyl(oxo)-λ4-sulfanium iodide | |
| Other names
Trimethylsulphoxonium iodide; Trimethyloxosulfonium iodide; S,S,S-Trimethylsulfoxonium iodide
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.015.641 |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C3H9IOS | |
| Molar mass | 220.07 g·mol−1 |
| Melting point | 208 to 212 °C (406 to 414 °F; 481 to 485 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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This compound is commercially available. It may be prepared by the reaction of dimethyl sulfoxide and iodomethane:[2]
- (CH3)2SO + CH3I → (CH3)3SO+I−
References
edit- ^ 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.