53731-16-1Relevant academic research and scientific papers
DISUBSTITUTED-AMINODIFLUOROSULFINIUM SALTS, PROCESS FOR PREPARING SAME AND METHOD OF USE AS DEOXOFLUORINATION REAGENTS
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Page/Page column 40-41, (2010/12/31)
The invention relates to disubstituted-aminodifluorosulfinium salts represented by the formula (I). Processes for preparing same and methods of use as deoxofluorinating reagent is also provided.
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.
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.
1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine: A new selective fluorinating agent
Petrov,Swearingen,Hong,Chris Petersen
, p. 25 - 31 (2007/10/03)
The title compound has been prepared in 96-98% yield by the reaction of tetrafluoroethylene and dimethylamine. 1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine (1) is found to be an effective reagent for the conversion of alcohols into alkyl fluorides. Reaction of 1 and primary alcohols proceeds with high yield formation of the corresponding alkyl fluorides at elevated temperature. However, the reaction of secondary and tertiary alcohols rapidly takes place at 0-10°C, producing corresponding alkyl fluorides as major product along with some olefins.
Variable-Temperature Fluorine-19 Nuclear Magnetic Resonance Spectra of Fluorocyclooctane
Weigert, F.J.,Middleton, W.J.
, p. 3289 - 3291 (2007/10/02)
Two conformational processes have been observed for fluorocyclooctane by variable-temperature, protondecoupled fluorine NMR.The observations are in good agreement with predictions by molecular mechanics of ring inversion and pseudorotation among nonequivalent boat-chairs.
