Trimethylsulfoxonium iodide

• Catalog No.: A14589
• CAS Number: 1774-47-6
• M. F.: C3H9IOS
• M. W.: 220.07243
• Purity: 98+%

SYNONYMS

• Title: 三甲基碘化亚砜
• IUPAC name: trimethyl(oxo)-λ^6-sulfanylium iodide
• IUPAC Traditional name: trimethyl(oxo)-λ^6-sulfanylium iodide

DATABASE IDS

• Beilstein Number: 3595854
• CAS Number: 1774-47-6
• EC Number: 217-204-2
• MDL Number: MFCD00011899

PROPERTIES

• Purity: 98+%
• Melting Point: ca 170°C dec.
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• RTECS: WS3585000
• Safety Statements: 26-37
• Storage Warning: Light Sensitive
• TSCA Listed: 是

REFERENCES

• Review of the chemistry of sulfonium ylides: Russ. Chem. Rev., 50, 481 (1981). Extensive review of the synthetic applications of dimethylsulfoxonium methylide: Tetrahedron, 43, 2609 (1987).
• For an example (conversion of cyclohexanone to the epoxide), see: Org. Synth. Coll., 5, 755 (1973). In contrast to Trimethylsulfonium iodide, A12639, reaction with ɑ?-unsaturated ketones occurs by 1,4-addition to give cyclopropanes: J. Am. Chem. Soc., 87, 1353 (1965):
  
• Reaction with epoxides gives oxetanes, unlike the sulfonium ylide which gives allylic alcohols: J. Org. Chem., 48, 5133 (1983); Synthesis, 1140 (1987); cf Tetrahedron Lett., 35, 5449 (1994):
  
• Similarly, N-arenesulfonylaziridines undergo ring expansion to azetidines with inversion at one carbon. Thus, cis-substituted aziridines give trans-azetidines and vice versa: Tetrahedron, 45, 1851 (1989):
  
• The ylide, generated with strong base, is a methylene transfer reagent.
• Efficient addition to enones has been effected with a highly basic system consisting of KOH in DMSO with a phase-transfer catalyst: Synth. Commun., 26, 1785 (1996).