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A12639 Trimethylsulfonium iodide, 99%

CAS Number
2181-42-2
Synonyms

Stock No. Size Price ($) Quantity Availability
A12639-18 50g 47.60
A12639-30 250g 199.00
A12639-0B 1000g 728.00
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Trimethylsulfonium iodide, 99%

MDL
MFCD00011632
EINECS
218-555-4

Chemical Properties

Formula
(CH3)3SI
Formula Weight
204.07
Melting point
ca 215° subl.
Storage & Sensitivity
Light Sensitive. Ambient temperatures.

Literature References

The ylide, generated with strong base, is a powerful methylene transfer reagent, converting aldehydes and ketones to epoxides; reaction with ɑß-enones also gives epoxides (contrast Trimethyl­sulfoxonium iodide, A14589): J. Am. Chem. Soc., 87, 1353 (1965):

/n

Other conditions for addition to aldehydes include: phase-transfer catalysis: Angew. Chem. Int. Ed., 12, 845 (1973), KOH in acetonitrile: Tetrahedron Lett., 23, 5283 (1982), or KF on alumina: Tetrahedron, 41, 1259 (1985). With aryl aldehydes, the use of KO-t-Bu gives improved results by suppressing the competing Cannizzaro reaction: Org. Prep. Proced. Int., 27, 219 (1995). A simplified, solvent-free method employing KO-t-Bu has been reported for ketones: Heterocycles, 46, 185 (1997). With excess of the sulfonium ylide, ketones or epoxides give good yields of allylic alcohols, whereas aldehydes give poor yields. Under similar conditions, the sulfoxonium ylide gives oxetanes: Tetrahedron Lett., 35, 2009, 5449 (1994).

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Methylene transfer to imines and arylhydrazones gives aziridines and N-arylaminoaziridines respectively: Synthesis, 330 (1983).

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Addition to vinyl sulfones gives cyclopropyl sulfones: J. Org. Chem., 29, 3277 (1964). Similarly, vinylsulfonates and sulfonamides give cyclopropanes in fair to good yields: J. Org. Chem., 33, 3849 (1968).

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Methylene transfer to allylic, propargylic, benzylic and primary alkyl halides and sulfonates results in formation of terminal alkenes in generally good yields: Tetrahedron Lett., 35, 5453 (1994).

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Reaction with Ag2O gives the corresponding hydroxide, which is a useful methylating agent for various functional groups, including carboxylic acids, phenols, thiols and N-heterocycles: J. Org. Chem., 44, 638 (1979). Both the iodide and the hydroxide have been used for the methylation of pyrimidine nucleosides; see, e.g.: J. Chem. Soc., Perkin 1, 13 (1989).

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Other References

Beilstein
3555192
Harmonized Tariff Code
2930.90
TSCA
Yes
RTECS
WR8750000

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