Trimethylsulfoxonium iodide
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| Preferred IUPAC name
Trimethyl(oxo)-λ4-sulfanium iodide | |
Other names
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3D model (JSmol)
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| ECHA InfoCard | 100.015.641 |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| [(CH3)3SO]+I− | |
| Molar mass | 220.07 g·mol−1 |
| Appearance | white solid |
| 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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Trimethylsulfoxonium iodide is an organosulfur compound with the chemical formula [(CH3)3S=O]+I−. It is a sulfoxonium salt derived from dimethylsulfoxide. It is iodide salt of a common sulfoxonium cation. This compound, a colorless solid, is commercially available. It may be prepared by the alkylation of dimethyl sulfoxide with iodomethane:[1]
- (CH3)2SO + CH3I → [(CH3)3SO]+I−
The trimethylsulfoxonium ion features a tetrahedral molecular geometry at sulfur center. The ion has idealized C3v symmetry. It is isoelectronic with trimethylphosphine oxide.
Trimethylsulfoxonium iodide is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride.[2] The latter compound is used to prepare epoxides from ketones and aldehydes.
References
[edit]- ^ 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.
- ^ Corey, E. J.; Chaykovsky, Michael. "Methylenecyclohexane Oxide". Organic Syntheses; Collected Volumes, vol. 5, p. 755.
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