Trimethylsulfoxonium iodide

Trimethylsulfoxonium iodide

Names
Preferred IUPAC name Trimethyl(oxo)-λ4-sulfanium iodide
Other names Trimethylsulphoxonium iodide; Trimethyloxosulfonium iodide; S,S,S-Trimethylsulfoxonium iodide
Identifiers
CAS Number	1774-47-6  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL283149  N
ChemSpider	67079  N
ECHA InfoCard	100.015.641
EC Number	217-204-2
PubChem CID	74498
CompTox Dashboard (EPA)	DTXSID001014581
InChI InChI=1S/C3H9OS.HI/c1-5(2,3)4;/h1-3H3;1H/q+1;/p-1 N Key: BPLKQGGAXWRFOE-UHFFFAOYSA-M N
SMILES O=[S+](C)(C)C.[I-]
Properties
Chemical formula	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). N  verify  (what is  YN ?) Infobox references

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 C_3v 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.