123933-37-9Relevant academic research and scientific papers
Fluorination of thiocarbon compounds with bis(2-methoxyethyl)aminosulfur trifluoride (deoxo-fluor reagent): A facile synthesis of gem-difluorides
Lal, Gauri S.,Lobach, Elyse,Evans, Ann
, p. 4830 - 4832 (2000)
A variety of thiocarbonyl derivatives (thioketone, thioester, thioamide, dithioester, and dithiocarbamate) were converted to the corresponding gem-difluorides in excellent yields on reaction with the fluorinating agent, bis(2-methoxyethyl)aminosulfur trif
Conversion of Esters to α,α-Difluoro Ethers using Bromine Trifluoride
Rozen, Shlomo,Mishani, Eyal
, p. 1761 - 1762 (1993)
Bromine trifluoride reacts rapidly with O-substituted thioesters to forms α,α-difluoro ethers, a family of almost unknown compounds.
Impact of fluorine substituents on the rates of nucleophilic aliphatic substitution and β-elimination
Martinez, Henry,Rebeyrol, Adele,Nelms, Taylor B.,Dolbier Jr., William R.
experimental part, p. 167 - 175 (2012/03/27)
A measure of the quantitative effect of proximate fluorine substituents on the rates of SN2 and E2 reactions has been obtained through a study mainly of reactions of fluorinated n-alkyl bromides with weak base, strong nucleophile azide ion and strong base/nucleophile methoxide ion in the protic solvent methanol and the aprotic solvent, DMSO. The order of reactivity for SN2 reactions of azide in methanol at 50 °C was found to be: n-alkyl-Br > n-alkyl-CHFBr > n-perfluoroalkyl-CH2CH 2Br n-perfluoroalkyl-CH2Br > n-alkyl-CF2Br. Approximate relative rates of reaction were: 1, 0.20, 0.12, 1 × 10 -4, -5. The order of reactivity for E2 reactions was found to be: n-perfluoroalkyl-CH2CH2Br n-alkyl-CF2Br > n-alkyl-CHFBr > n-alkyl-Br. The approximate relative rates for reaction of methoxide in methanol at 50 °C were: 1100, 4.4, 1.9, 1.
Arylsulfur chlorotetrafluorides as useful fluorinating agents: Deoxo- and dethioxo-fluorinations
Umemoto, Teruo,Singh, Rajendra P.
experimental part, p. 17 - 27 (2012/09/07)
Usage of arylsulfur chlorotetrafluorides 1 as versatile deoxo- and dethioxo-fluorinating agents is described. There have been developed two convenient methods for the in situ preparation of reactive arylsulfur trifluorides 2 from 1. The one is reduction of 1 with a reducer such as pyridine to 2, and the other is disproportionation of 1 with a diaryl disulfide to 2 with evolution of chlorine gas. The latter method is a convenient way to get neat 2 from 1. The in situ prepared 2 fluorinates many kinds of substrates such as alcohols, aldehydes, ketones, diketones, and carboxylic acids to give the corresponding CF, CF2, CF2CF2, and CF 3 compounds in high yields. 2 also fluorinates various sulfur compounds including CS groups to give CF2, OCF2, CF 3, and OCF3 compounds in high yields. Reactions of 2 with diols or bis(trimethylsilyl) derivatives of diols or amino alcohols provided the corresponding deoxofluoro-arylsulfinylation products in high yields. In addition, it has been found that chlorotetrafluorides 1 directly and effectively react with the sulfur compounds to give the corresponding fluoro compounds in high yields. Since they are the intermediates for the production of industrially useful arylsulfur pentafluorides, arylsulfur chlorotetrafluorides 1, in particular, phenylsulfur chlorotetrafluoride (1a) are expected to find use as inexpensive and versatile deoxo- and dethioxo-fluorinating agents for the preparation of many organofluoro compounds.
FLUORINATION PROCESSES WITH ARYLSULFUR HALOTETRAFLUORIDES
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Page/Page column 41; 42, (2009/10/22)
New fluorination processes for introducing one or more fluorine atoms into target substrate compounds with arylsulfur halotetrafluorides are disclosed. Also disclosed are methods for preparation of arylsulfur trifluorides.
METHODS AND COMPOSITIONS FOR PRODUCING DIFLUOROMETHYLENE-AND TRIFLUOROMETHYL-CONTAINING COMPOUNDS
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Page/Page column 28, (2009/07/17)
New methods for producing difluoromethylene-containing compounds with phenylsulfur trifluoride or a primary alkyl-substituted phenylsulfur trifluoride are disclosed. Also, new methods for producing trifluoromethyl-containing compounds with phenylsulfur trifluoride or primary alkyl-substituted phenylsulfur trifluoride are also disclosed.
Bis(2-methoxyethyl)aminosulfur trifluoride: A new broad-spectrum deoxofluorinating agent with enhanced thermal stability
Lal, Gauri S.,Pez, Guido P.,Pesaresi, Reno J.,Prozonic, Frank M.,Cheng, Hansong
, p. 7048 - 7054 (2007/10/03)
Bis(2-methoxyethyl)aminosulfur trifluoride, (CH3OCH2CH2)2NSF3 (Deoxo-Fluor reagent), is a new deoxofluorinating agent that is much more thermally stable than DAST (C2H5)2NSF3 and its congeners. It is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gem-difluorides, and carboxylic acids to the trifluoromethyl derivatives with, in some cases, superior performance compared to DAST. The enhanced stability is rationalized on the basis of conformational rigidity imposed by a coordination of the alkoxy groups with the electron-deficient sulfur atom of the trifluoride.
