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.
Bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor™) is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gemdifluorides 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.-The title agent shows a greater range and scope of applicability than DAST. -(LAL, GAURI S.; PEZ, GUIDO P.; PESARESI, RENO J.; PROZONIC, FRANK M.; CHENG, HANSONG;
Bis(2-methoxyethyl)aminosulfur Trifluoride: A New Broad-Spectrum Deoxofluorinating Agent with Enhanced Thermal Stability.-The easily available title compound (II) proves to be an effective reagent for the facile conversion of alcohols (III) and sugars (V) to corresponding alkyl fluorides [(IV) and (VI)], aldehydes and ketones (VII) to the corresponding gem-difluorides (VIII), and carboxylic acids (IX) to their trifluoromethyl derivatives (XI) via acyl fluorides (X). It is a less thermally sensitive, broader-spectrum alternative to the traditional dialkylaminosulfur trifluoride (DAST) deoxofluorination reagents.-(LAL, GAURI S.; PEZ, GUIDO P.; PESARESI, RENO J.; PROZONIC, FRANK M.; Chem.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.