I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
Stock No. | Size | Price ($) | Quantity | Availability |
---|---|---|---|---|
A14589-14 | 25g | 17.80 |
|
|
A14589-22 | 100g | 41.10 |
|
|
A14589-36 | 500g | 140.00 |
|
|
Trimethylsulfoxonium iodide reacts with sodium hydride to prepare dimethyloxosulfonium methylide, which is used as a methylene-transfer reagent in synthetic chemistry. It is used to prepare ylide, which reacts with carbonyl compounds to get epoxides. Further, it reacts with alfa,beta-unsaturated esters to get cyclopropyl esters.
The ylide, generated with strong base, is a methylene transfer reagent.
For an example (conversion of cyclohexanone to the epoxide), see: Org. Synth. Coll., 5, 755 (1973). In contrast to Trimethylsulfonium iodide, A12639, reaction with ɑß-unsaturated ketones occurs by 1,4-addition to give cyclopropanes: J. Am. Chem. Soc., 87, 1353 (1965):
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).
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):
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).
Sathishkumar, S.; Mahasampathgowri, S.; Balasubramanian, K. K.; Saiganesh, R. A convenient synthesis of dialkyl 2-(2-haloethylidene)malonates, cyanoacetates and halocrotonates by one carbon extension. Tetrahedron Lett. 2015, 56 (26), 4031-4035.
Kagawa, N.; Suzuki, M.; Kogure, N.; Toume, K. Characterization of organic iodides with iodine-127 nuclear magnetic resonance spectroscopy. Tetrahedron Lett. 2015, 56 (42), 5795-5798.
Hazard Statements: H319
Causes serious eye irritation.
Precautionary Statements: P264b-P280i-P305+P351+P338
Wash face, hands and any exposed skin thoroughly after handling Wear eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.