Abstract

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.

Keywords

ChemistryBroad spectrumThermal stabilitySpectrum (functional analysis)TrifluorideCombinatorial chemistryOrganic chemistry

Affiliated Institutions

Related Publications

Publication Info

Year
1999
Type
article
Volume
64
Issue
19
Pages
7048-7054
Citations
393
Access
Closed

External Links

View on DOI.org

Social Impact

Altmetric
PlumX Metrics

Social media, news, blog, policy document mentions

Citation Metrics

393
OpenAlex

Cite This

G. S. LAL, Guido P. Pez, Reno J. Pesaresi et al. (1999). Bis(2-methoxyethyl)aminosulfur Trifluoride:  A New Broad-Spectrum Deoxofluorinating Agent with Enhanced Thermal Stability. The Journal of Organic Chemistry , 64 (19) , 7048-7054. https://doi.org/10.1021/jo990566+

Identifiers

DOI
10.1021/jo990566+