19422-34-5Relevant academic research and scientific papers
A Novel Carbonyl to CF2 Transformation Using BrF3
Rozen, Shlomo,Mishani, Eyal,Bar-Haim, Arie
, p. 2918 (1994)
This work demonstrates that BrF3 is very efficient in converting various carbonyls through their azines, oxime methyl ethers, or various hydrazones into the corresponding CF2 moiety.
Aminodifluorosulfinium salts: Selective fluorination reagents with enhanced thermal stability and ease of handling
Lheureux, Alexandre,Beaulieu, Francis,Bennett, Christopher,Bill, David R.,Clayton, Simon,Laflamme, Franois,Mirmehrabi, Mahmoud,Tadayon, Sam,Tovell, David,Couturier, Michel
supporting information; experimental part, p. 3401 - 3411 (2010/07/07)
Diethylaminodifluorosulfinium tetrafluoroborate (XtalFluor-E) and morpholinodifluorosulfinium tetrafluoroborate (XtalFluor-M) are crystalline fluorinating agents that are more easily handled and significantly more stable than Deoxo-Fluor, DAST, and their analogues. These reagents can be prepared in a safer and more cost-efficient manner by avoiding the laborious and hazardous distillation of dialkylaminosulfur trifluorides. Unlike DAST, Deoxo-Fluor, and Fluolead, XtalFluor reagents do not generate highly corrosive free-HF and therefore can be used in standard borosilicate vessels. When used in conjunction with promoters such as Et3N3HF, Et3N2HF, or DBU, XtalFluor reagents effectively convert alcohols to alkyl fluorides and carbonyls to gem-difluorides. These reagents are typically more selective than DAST and Deoxo-Fluor and exhibit superior performance by providing significantly less elimination side products.
Reaction of chlorosulfonyl isocyanate with fluorosubstituted alkenes: Evidence of a concerted pathway
Shellhamer, Dale F.,Davenport, Kevyn J.,Hassler, Danielle M.,Hickle, Kelli R.,Thorpe, Jacob J.,Vandenbroek, David J.,Heasley, Victor L.,Boatz, Jerry A.,Reingold, Arnold L.,Moore, Curtis E.
experimental part, p. 7913 - 7916 (2011/02/25)
Concerted reactions are indicated for the electrophilic addition of chlorosulfonyl isocyanate with monofluoroalkenes. A vinyl fluorine atom on an alkene raises the energy of a stepwise transition state more than the energy of the competing concerted pathw
Aminodifluorosulfinium Tetrafluoroborate salts as stable and crystalline deoxofluorinating reagents
Beaulieu, Francis,Beauregard, Louis-Philippe,Courchesne, Gabriel,Couturier, Michel,Laflamme, Francois,L'Heureux, Alexandre
supporting information; experimental part, p. 5050 - 5053 (2009/12/28)
Aminodifluorosulfinium tetrafluoroborate salts were found to act as efficient deoxofluorinating reagents when promoted by an exogenous fluoride source and, In most cases, exhibited greater selectivity by providing less elimination byproduct as compared to DAST and DeoxoFluor. Aminodifluorosulfinium tetrafluoroborates are easy handled crystalline salts that show enhanced thermal stability over dialkylaminosulfur trifluorides, are storage-stable, and unlike DAST and Deoxo-Fluor do not react violently with water.
Process for producing alpha, alpha-difluorocycloalkane compound
-
, (2008/06/13)
A method for producing an α,α-difluorocycloalkane at high purity with good efficiency, which comprises a step of treating a fluorocycloalkene with hydrogen fluoride wherein the fluorocycloalkene has one fluorine atom directly bonded to a carbon atom of carbon-carbon unsaturated double bond, more preferably, a step of directly adding the hydrogen fluoride to a reaction mixture obtained by treating the cycloalkanone with the de-oxygen fluorinating agent.
Fluorination with aminosulfur trifluorides
-
, (2008/06/13)
A fluorination method of oxygen and halogen sites with diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating reagents is disclosed.
Thermally stable aminosulfur trifluorides
-
, (2008/06/13)
Diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating agents are disclosed.
Fluorination with aminosulfur trifluorides
-
, (2008/06/13)
A fluorination method of oxygen and halogen sites with diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating reagents is disclosed.
Bis(2-methoxyethyl)aminosulfur trifluoride: A new broad-spectrum deoxofluorinating agent with enhanced thermal stability
Lal, Gauri S.,Fez, Guido P.,Pesaresi, Reno J.,Prozonic, Frank M.
, p. 215 - 216 (2007/10/03)
Bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor) is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gem-difluorides and also for the transformation of carboxylic acids to their trifluoromethyl derivatives; it is a less thermally sensitive, broader-spectrum alternative to the traditional dialkylaminosulfur trifluoride (DAST) deoxofluorination reagents.
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.
