Misplaced Pages

Trimethylsulfoxonium iodide

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
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)-λ-sulfanium iodide
Other names Trimethylsulphoxonium iodide; Trimethyloxosulfonium iodide; S,S,S-Trimethylsulfoxonium iodide
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.015.641 Edit this at Wikidata
EC Number
  • 217-204-2
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H9OS.HI/c1-5(2,3)4;/h1-3H3;1H/q+1;/p-1Key: BPLKQGGAXWRFOE-UHFFFAOYSA-M
SMILES
  • O=(C)(C)C.
Properties
Chemical formula C3H9IOS
Molar mass 220.07 g·mol
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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:

(CH3)2SO + CH3I → (CH3)3SOI

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. 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.
Categories:
Trimethylsulfoxonium iodide Add topic