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1774-47-6 - Trimethylsulfoxonium iodide, 98+% - A14589 - Alfa Aesar

A14589 Trimethylsulfoxonium iodide, 98+%

Codice CAS
1774-47-6
Sinonimi

Dimensioni Prezzo ($) Quantità Disponibilità
25g 17,20
100g 39,10
500g 133,00
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Trimethylsulfoxonium iodide, 98+%

MDL
MFCD00011899
EINECS
217-204-2

Proprietà chimiche

Formula
(CH3)3SOI
Peso formula
220.07
Punto di fusione
ca 170° dec.
Sensibilità
Light Sensitive
Solubilità
Soluble in water.

Applicazioni

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.

Note

Incompatible with strong oxidizing agents and strong bases. Light sensitive.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Dichiarazioni precauzionali: P261-P280a-P305+P351+P338-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
3595854
Codice tariffe armonizzato
2930.90
TSCA
Yes
RTECS
WS3585000

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