1493-13-6Relevant articles and documents
REACTIVITE DES ESTERS SULFONIQUES ET PYROSULFONIQUES PERFLUORES RFSO3RF ET RFSO3SO3RF. HETEROLYSE DE LA LIAION S-O
Oudrhiri-Hassani, M.,Brunel, D.,Germain, A
, p. 163 - 178 (1986)
Perfluoroalkyl perfluoroalkanesulfonates RFSO3R'F (RF, R'F = CF3, C2F5) and perfluoroalkyl perfluoroalkanepyrosulfonates RFSO3SO3RF, mixed with perfluoroalkanesulfonic acids (CF3SO3H or C2F5SO3H) decompose thermally.Depending on the starting materials, different products result from nucleophilic attack of a perfluoroalkanesulfonate anion of the acid on the sulfur atom of the sulfonate group of the ester, with heterolysis of the S-O bond.Therefore, under these conditions, the perfluorinated esters are not perfloroalkylating agents, but rather perfluorosulfonylating agents.
The vibrational spectrum of trifluoromethanesulphonic acid, CF3SO3H, and the determination of its degrees of discociation in aqueous solution by Raman spectroscopy
Edwards, H. G. M.
, p. 715 - 720 (1989)
The Raman and i.r. spectra of trifluoromethanesulphonic acid, CF3SO3H, have been obtained, and vibrational assignments made which are consistent with Cs molecular symmetry.The degrees of dissociation of CF3SO3H in aqueous solution in the concentration range 1.8-11.1 M were determined from Raman intensity measurements on the Δν = 1034 cm-1 band characteristic of the CF3SO3- ion.The results confirm that CF3SO3H is more dissociated into CF3SO3- ions than CH3SO3H is into CH3SO3- at similar concentrations.A limiting value of Kc = 280 mol dm-3 is calculated for low acid concentrations of CF3SO3H.
Perfluoroalkanesulfonylimids and their lithium salts: Synthesis and characterisation of intermediates and target compounds
Conte, Lino,Gambaretto, Gian Paolo,Caporiccio, Gerardo,Alessandrini, Fabrizio,Passerini, Stefano
, p. 243 - 252 (2004)
ECF processes have been extensively experienced and developed since early 1970s at the Fluorine Chemistry Laboratory of Padua University: several classes of perfluorinated inert and functional compounds have been obtained, in particular perfluoro heterocyclics and perfluorinated acid fluorides.Recently the demand for electrolyte salts, applied in lithium batteries, drove our interest to investigate on the perfluoroalkanesulfonylimides.A series of the perfluoroalkanesulfonylfluoride precursors has been obtained by ECF and their metathesis to the related imides and lithium salts has been investigated.A number of representative products has been obtained and characterized in their structure and ionic conductivity.
Thermodynamics of methanesulfonic acid revisited
Guthrie,Gallant
, p. 1295 - 1298 (2000)
Recently we reported a study of the thermodynamics of methanesulfonic acid and some of its derivatives. The foundation of these results was a measurement of the heat of reaction of S-methyl thioacetate with aq sodium hypochlorite, leading to methanesulfonic acid. We have reinvestigated this reaction and discovered that contrary to the initial stoichiometry experiments, the stoichiometry under the reaction conditions is not as was believed and that the heat of reaction observed was spuriously high. We have found a new reaction, that of sulfite ion with methyl methanesulfonate, which does allow a clean determination of the heat of formation of methanesulfonic acid. Revised thermodynamic quantities for methanesulfonic acid, methanesulfonyl chloride, and methyl methanesulfonate are reported here.
Photoinduced and Thermally Induced Rearrangements in a Thianthrenium Salt System
Saeva, Franklin D.
, p. 37 - 39 (1987)
A low-lying ?* level localized on a sulphur-carbon moiety in p-cyanobenzylthianthrenium trifluoromethanesulphonate allows facile photoinduced molecular rearrangements to occur via an in-cage fragmentation-recombination mechanism involving cation-radical-radical intermediates.
SYNTHESIS OF TRIFLUOROMETHANESULFONATE ESTERS BY REATION OF ALKYL CHLORIDES WITH CHLORINE (I) AND BROMINE (I) TRIFLUOROMETHANESULFONATE
Katsuhara,Yutaka,Desmarteau, Darryl D.
, p. 257 - 264 (1980)
The synthesis of the first trifluoromethanesulfonate esters of the type CF3SO3(CH2)nO3SCF3(n=1,2,3) are reported.The new compounds are prepared from Cl(CH2)nCl by substitutive electrophilic dehalogenation reactions with CF3SO2OX (x=Cl,Br).The extension of this reaction to HCCl3 results in HC(O3SCF3)3 but the compound is unstable at 22 deg.
Remarkable Acid Catalysis in Proton-Coupled Electron-Transfer Reactions of a Chromium(III)-Superoxo Complex
Devi, Tarali,Lee, Yong-Min,Nam, Wonwoo,Fukuzumi, Shunichi
, p. 8372 - 8375 (2018)
Much enhanced acid catalysis was observed in oxygen atom transfer (OAT) reactions by a mononuclear nonheme Cr(III)-superoxo complex, [(Cl)(TMC)CrIII(O2)]+ (1), in the presence of triflic acid. In the acid-catalyzed reactions, the reactivity of 1 in OAT of thioanisole was enhanced significantly, showing more than 104-fold acceleration in rate. Electron transfer (ET) from electron donors to 1 also occurred only in the presence of HOTf. The enhanced reactivity of 1 by HOTf was explained by proton-coupled electron transfer from electron donors, such as ferrocene, to 1 in light of the Marcus theory of ET. The present study reports for the first time the dramatic proton effect on the chemical properties of metal-superoxo species.
Synthesis of trifluoromethanesulfonic acid from CHF3
Mukhopadhyay, Sudip,Bell, Alexis T.,Vijay Srinivas,Smith, Gary S.
, p. 660 - 662 (2004)
Trifluoromethane is transformed to trifluoromethanesulfonic acid (TFMSA) at low temperature in a liquid-phase reaction in a strong acid such as fuming sulfuric acid as well as in a strong basic solution such as t-BuOK/DMF.
Water determines the products: An unexpected Br?nsted acid-catalyzed PO-R cleavage of P(iii) esters selectively producing P(O)-H and P(O)-R compounds
Li, Chunya,Wang, Qi,Zhang, Jian-Qiu,Ye, Jingjing,Xie, Ju,Xu, Qing,Han, Li-Biao
supporting information, p. 2916 - 2922 (2019/06/18)
Water is found able to determine the selectivity of Br?nsted acid-catalyzed C-O cleavage reactions of trialkyl phosphites: with water, the reaction quickly takes place at room temperature to afford quantitative yields of H-phosphonates; without water, the reaction selectively affords alkylphosphonates in high yields, providing a novel halide-free alternative to the famous Michaelis-Arbuzov reaction. This method is general as it can be readily extended to phosphonites and phosphinites and a large scale reaction with much lower loading of the catalyst, enabling a simple, efficient, and practical preparation of the corresponding organophosphorus compounds. Experimental findings in control reactions and substrate extension as well as preliminary theoretical calculation of the possible transition states all suggest that the monomolecular mechanism is preferred.
METHOD FOR PREPARING OXYSULPHIDE AND FLUORINATED DERIVATIVES IN THE PRESENCE OF AN ORGANIC SOLVENT
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Paragraph 0193-0195, (2019/04/05)
The present invention concerns a method for preparing an oxysulphide and fluorinated derivative of formula (III) Ea-SO3R (III) that comprises bringing a compound of formula (II) Ea-SOOR (II)—Ea representing the fluorine atom or a group having 1 to 10 carbon atoms chosen from the fluoroalkyls, the perfluoroalkyls and the fluoroalkenyls; and—R representing hydrogen, a monovalent cation or an alkyl group; into contact, in the presence of a polar aprotic organic solvent, with an oxidising agent.
