NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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trimethyl(oxo)-$l^{6}-sulfanylium iodide
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trimethyl(oxo)-λ6-sulfanylium iodide
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IUPAC Traditional name
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trimethyl(oxo)-$l^{6}-sulfanylium iodide
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trimethyl(oxo)-λ6-sulfanylium iodide
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Synonyms
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Trimethyl(oxo)sulphonium iodide
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Trimethylsulphoxonium iodide
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Trimethylsulphoxonium iodide
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Trimethyloxosulfonium iodide
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Trimethylsulfoxonium iodide
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Trimethylsulfoxonium iodide
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三甲基碘化亚砜
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CAS Number
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EC Number
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MDL Number
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Beilstein Number
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PubChem SID
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PubChem CID
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Wikipedia Title
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
H Acceptors
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1
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H Donor
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0
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LogD (pH = 5.5)
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-2.5195513
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LogD (pH = 7.4)
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-2.5195513
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Log P
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-2.5195513
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Molar Refractivity
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24.539 cm3
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Polarizability
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10.235904 Å3
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Polar Surface Area
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17.07 Å2
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Rotatable Bonds
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0
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Lipinski's Rule of Five
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true
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DETAILS
DETAILS
Wikipedia
Sigma Aldrich
Sigma Aldrich -
T80500
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Packaging 25, 100, 500 g in glass bottle Application Treatment with strong base yields the ylide which adds to the carbonyl group of ketones1 and aldehydes2,3 to give epoxides. Also adds preferentially to the double bond of α,β-unsaturated esters to give cyclopropyl esters.4,5 |
Sigma Aldrich -
92763
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Other Notes Precursor of dimethylsulfoxonium methylide, a versatile C1-reagent1,2 |
REFERENCES
REFERENCES
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PubMed
Google Books
- • 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).
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PATENTS
PATENTS
PubChem Patent
Google Patent