Structure of (CH3)3S+. The C-S-C angles are 102° and C-S bond distance is 177 picometers.[1]
In organic chemistry, a sulfonium ion, also known as sulphonium ion or sulfanium ion, is a positively-charged ion (a "cation") featuring three organic substituents attached to sulfur. These organosulfur compounds have the formula [SR3]+. Together with a negatively-charged counterion, they give sulfonium salts. They are typically colorless solids that are soluble in organic solvent.[2][3]
^Knop, Osvald; Cameron, T. Stanley; Bakshi, Pradip K.; Linden, Antony; Roe, Stephen P. (1994). "Crystal Chemistry of Tetraradial Species. Part 5. Interaction Between Cation Lone Pairs and Phenyl Groups in Tetraphenylborates: Crystal Structures of Me3S+, Et3S+, Me3SO+, Ph2I+, and 1-Azoniapropellane Tetraphenylborates". Canadian Journal of Chemistry. 72 (8): 1870–1881. doi:10.1139/v94-238.
^C. J. M. Stirling, ed. (1981). The Sulphonium Group: Part 1, Volume 1. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. doi:10.1002/9780470771648. ISBN 9780470771648.C. J. M. Stirling, ed. (1981). The Sulphonium Group: Part 2, Volume 2. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. doi:10.1002/9780470771655. ISBN 9780470771655.
^Kozhushkov, Sergei I.; Alcarazo, Manuel (2020). "Synthetic Applications of Sulfonium Salts". European Journal of Inorganic Chemistry. 2020 (26): 2486–2500. doi:10.1002/ejic.202000249. PMC 7386937. PMID 32742188.
In organic chemistry, a sulfonium ion, also known as sulphonium ion or sulfanium ion, is a positively-charged ion (a "cation") featuring three organic...
respectively. Deprotonation of sulfonium and oxosulfonium salts affords ylides, of structure R2S+−C−−R′2 and R2S(O)+−C−−R′2. While sulfonium ylides, for instance...
with metal ions like palladium and platinum. Other common ylides include sulfonium ylides and sulfoxonium ylides; for instance, the Corey-Chaykovsky reagent...
monoxide and producing chloro(dimethyl)sulfonium chloride, 4. After addition of the alcohol 5, the chloro(dimethyl)sulfonium chloride 4 reacts with the alcohol...
The TASF reagent or tris(dimethylamino)sulfonium difluorotrimethylsilicate is a reagent in organic chemistry with structural formula [((CH3)2N)3S]+[F2Si(CH3)3]−...
DMSO is used as a mild oxidant. It forms the basis of several selective sulfonium-based oxidation reactions including the Pfitzner–Moffatt oxidation, Corey–Kim...
reaction epoxides are generated from carbonyl groups and sulfonium ylides. In this reaction, a sulfonium is the leaving group instead of chloride. Electron-deficient...
developed based on solvent participation or the formation of bicyclic sulfonium ions as chiral-auxiliary groups. The non-enzymatic glycosylation is also...
condensation. Other carbon acids susceptible to deprotonation by NaH include sulfonium salts and DMSO. NaH is used to make sulfur ylides, which in turn are used...
1957). "Synthesis of Certain 3-Hydroxy-3-phenylpropylsulfonium Salts. Sulfonium Analogs of Artane (Trihexyphenidyl) and Pathilon (Tridihexethyl Iodide)"...
the conjugate base of the thiol. Thioethers undergo alkylation to give sulfonium ions. Alcohols alkylate to give ethers: R − OH + R ′ − X ⟶ R − O − R ′...
warming to room temperature, the base will deprotonate the sulfonium ion creating the sulfonium ylide 4, which quickly undergoes a [2,3]-sigmatropic rearrangement...
S2CID 38134977. Rhodes D, Hanson AD (1993). "Quaternary Ammonium and Tertiary Sulfonium Compounds in Higher Plants". Annual Review of Plant Physiology and Plant...
Service Double Master of Science, an academic degree Methyl methionine sulfonium chloride Master of Medical Science, an academic degree Master of Management...
chloride ions by intramolecular nucleophilic substitution to form cyclic sulfonium ions. These very reactive intermediates tend to permanently alkylate nucleotides...
(diazomethyl)phosphonate Johnson–Corey–Chaykovsky reaction Epoxide Reagent: a sulfonium ylide Oxo-Diels–Alder reaction Pyran Aldehydes can, typically in the presence...
5′ carbon) attached to the sulfur of methionine, therefore making it a sulfonium cation (i.e., three substituents and positive charge). The sulfur acts...
base gives thiolate ions. Thioethers are the sulfur analogs of ethers. Sulfonium ions have three groups attached to a cationic sulfur center. Dimethylsulfoniopropionate...
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