- PARTIELL NICHTFLUORIERTE VERBINDUBGEN BEI DER ELECTROCHEMISCHEN FLUORIRUNG VON SULFOLEN
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The sulfonylfluorides C3F7CHFSO2F and C3F7CH2SO2F have been isolated and characterized as byproducts of the electrochemical fluorination of 2,5-dihydrothiophene-1,1-dioxide (sulfolene).A mechanism is given for the formation of these byproducts.
- Geisler, Klaus,Koemm, Ulrich,Metzinger, Hans-Gerd
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Read Online
- Trifluoromethyl Nonaflate: A Practical Trifluoromethoxylating Reagent and its Application to the Regio- and Stereoselective Synthesis of Trifluoromethoxylated Alkenes
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The trifluoromethoxy group has elicited much interest among drug and agrochemical discovery teams because of its unique properties. We developed trifluoromethyl nonafluorobutanesulfonate (nonaflate), TFNf, an easy-to-handle, bench-stable, reactive, and scalable trifluoromethoxylating reagent. TFNf is easily and safely prepared in a simple process in large scale and the nonaflyl part of TFNf can easily be recovered as nonaflyl fluoride after usage and recycled. The synthetic potency of TFNf was showcased with the underexplored synthesis of various trifluoromethoxylated alkenes, through a high regio- and stereoselective hydro(halo)trifluoromethoxylation of alkyne derivatives such as haloalkynes, alkynyl esters, and alkynyl sulfones. The synthetic merits of TFNf were further underscored with a high-yielding and smooth nucleophilic trifluoromethoxylation of alkyl triflates/bromides and primary/secondary alcohols.
- Hammond, Gerald B.,Kumon, Tatsuya,Lu, Zhichao,Umemoto, Teruo
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supporting information
p. 16171 - 16177
(2021/06/27)
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- N-oxide of perfluorobutylsulfonyl(3-dimethylaminopropyl)amine as well as preparation method and application thereof
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The invention discloses an N-oxide of perfluorobutylsulfonyl(3-dimethylaminopropyl)amine as well as a preparation method and application of the N-oxide, and belongs to the field of fluorine-containingfine chemicals. According to the invention, the perfluorobutylsulfonyl(3-dimethylaminopropyl)amine is produced by a one-pot method and serves as a aqueous film-forming foam extinguishing agent, wherein the product is prepared by reacting perfluorobutyl sulfonyl fluoride, alkyl diamine, a solvent, an acid-binding agent and an oxidant, and filtering the components to remove byproduct hydrochlorideand a distillation solvent, thereby obtaining the product. The method has the advantages of few production steps, shortened reaction time, low cost, reduced three wastes, no pollution, high yield andgood quality.
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Paragraph 0022; 0024; 0028; 0032
(2021/01/12)
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- PRODUCTION METHOD OF AMMONIUM PERFLUOROALKANE SULFONAMIDE
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PROBLEM TO BE SOLVED: To provide a production method of ammonium perfluoroalkane sulfonamide, which has high generation rate and high utilization efficiency of raw materials. SOLUTION: A production method of ammonium perfluoroalkane sulfonamide is selected which includes: an electrolytic fluorination step to obtain a product gas including perfluoroalkanesulfonyl fluoride by electrolytic fluorination of an alkane sulfonyl halide or tetrahydrothiophene-1,1-dioxide in anhydrous hydrogen fluoride; and a product gas reaction step to bring the product gas into contact with ammonia water and obtain a reaction liquid, in which the produced ammonium perfluoroalkane sulfonamide is dissolved and exists in the ammonia water, in which the electrolytic fluorination step and the product gas reaction step are conducted continuously, and simultaneously the amount of ammonia in the reaction liquid is maintained in a range of 3-12 pts.mass based on 100 pts.mass of the reaction liquid. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0076-0077
(2018/06/12)
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- METHOD FOR RECOVERING SULFONIC ESTERS OR SULFONYL HALIDES FROM SALTS OF SULFONIC ACIDS
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A method for the obtainment of an ester or a halide of a fluorinated sulfonic acid from an salt of a sulfonic acid is herein disclosed. The method is particularly useful for recovering waste sulfonate salts from reaction mixtures obtained by reaction of sulfonic esters of alcohols having a pKa lower than 15 with nucleophile compounds.
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Paragraph 0096-0099
(2017/02/24)
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- New synthesis of polyfluoroalkanesulfonylureas
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This study describes a new synthesis of F-alkanesulfonyl ureas by reaction of the sodium salt of perfluoroalkane sulfonamide (RF = C4F9, C6F13) with some isocyanates in anhydrous THF. The perfluorinated sulfonylureas are obtained, in one step, from moderate to good yields.
- Benfodda,Delon,Guillen,Blancou
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p. 1353 - 1358
(2008/09/18)
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- Perfluoroalkanesulfonylimids and their lithium salts: Synthesis and characterisation of intermediates and target compounds
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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.
- Conte, Lino,Gambaretto, Gian Paolo,Caporiccio, Gerardo,Alessandrini, Fabrizio,Passerini, Stefano
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p. 243 - 252
(2007/10/03)
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- Carbon-chain isomerization during the electrochemical fluorination in anhydrous hydrogen fluoride - A mechanistic study
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The compounds i-C4H9SO2F, i-C3H7SO2F and cyclo-C3 H7C(O)F have been subjected to electrochemical fluorination in anhydrous hydrogen fluoride. The resulting products were fully analyzed by NMR spectroscopy. From the reaction balances, literature data and quantum chemical calculations, a new mechanism for carbon-chain isomerization during the electrochemical fluorination (ECF) is proposed. The key step in the formation of isomeric products is believed to be a ring closure reaction involving carbo-cationic or biradical intermediates.
- Ignat'ev, Nikolai V.,Welz-Biermann, Urs,Heider, Udo,Kucheryna, Andriy,von Ahsen, Stefan,Habel, Wolfgang,Sartori, Peter,Willner, Helge
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- Die elektrochemische fluorierung von alkansulfonamiden und alkandisulfonamiden
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Alkane sulphonylamides and disulphonylamides are stable in anhydrous (HF)x and undergo quantitative fission of S-N bonds during electrochemical fluorination. Besides NF3, the corresponding perfluoroalkane sulphonyl fluorides and disulphonyl fluorides are formed.
- Satori,Juenger
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- SYNTHESIS OF PERFLUOROPROPANE-1,3-DISULFONIC ACID AND PERFLUOROBUTANE-1,4-DISULFONIC ACID
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Perfluoropropane-1,3-disulfonic acid, HO3S-(CF2)3-SO3H, and perfluorobutane-1,4-disulfonic acid, HO3S-(CF2)4-SO3H, have been prepared electrochemically from the alkanedisulfonyl difluorides.Whereas perfluoroalkanemonosulfonyl fluorides can easily be prepared via electrochemical fluorination the situation with disulfonyl difluorides is somewhat more difficult.NMR data are reported for all compounds.
- Herkelmann, R.,Sartori, P.
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p. 299 - 308
(2007/10/02)
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