Bis(2-methoxyethyl)aminosulfur trifluoride: A new broad-spectrum deoxofluorinating agent with enhanced thermal stability

Citation
Gs. Lal et al., Bis(2-methoxyethyl)aminosulfur trifluoride: A new broad-spectrum deoxofluorinating agent with enhanced thermal stability, J ORG CHEM, 64(19), 1999, pp. 7048-7054
Citations number
38
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
19
Year of publication
1999
Pages
7048 - 7054
Database
ISI
SICI code
0022-3263(19990917)64:19<7048:BTANBD>2.0.ZU;2-#
Abstract
Bis(2-methoxyethyl)aminosulfur trifluoride, (CH3OCH2CH2)(2)NSF3 (Deoxo-Fluo r reagent), is a new deoxofluorinating agent that is much more thermally st able than DAST (C2H5)(2)NSF3 and its congeners. It is effective for the con version of alcohols to alkyl fluorides, aldehydes/ketones to the correspond ing gem-difluorides, and carboxylic acids to the trifluoromethyl derivative s with, in some cases, superior performance compared to DAST. The enhanced stability is rationalized on the basis of conformational rigidity imposed b y a coordination of the alkoxy groups with the electron-deficient sulfur at om of the trifluoride.