Trimethylsulfoxonium iodide

Trimethylsulfoxonium iodide
Skeletal formulas of the trimethylsulfoxonium cation and the iodide anion
Space-filling models of the component ions of trimethylsulfoxonium iodide
Names
Preferred IUPAC name
Trimethyl(oxo)-λ4-sulfanium iodide
Other names
Trimethylsulphoxonium iodide; Trimethyloxosulfonium iodide; S,S,S-Trimethylsulfoxonium iodide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.015.641 Edit this at Wikidata
EC Number
  • 217-204-2
  • InChI=1S/C3H9OS.HI/c1-5(2,3)4;/h1-3H3;1H/q+1;/p-1 ☒N
    Key: BPLKQGGAXWRFOE-UHFFFAOYSA-M ☒N
  • O=[S+](C)(C)C.[I-]
Properties
C3H9IOS
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 a sulfoxonium salt derived from dimethylsulfoxide. It is iodide salt of a common sulfoxonium ions. 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 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

  1. ^ 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.
  2. ^ Corey, E. J.; Chaykovsky, Michael. "Methylenecyclohexane Oxide". Organic Syntheses; Collected Volumes, vol. 5, p. 755.