Bis(2-methoxyethyl)aminosulfur Trifluoride: A New Broad-Spectrum Deoxofluorinating Agent with Enhanced Thermal Stability

Gauri S. Lal,* Guido P. Pez, Reno J. Pesaresi, Frank M. Prozonic and Hansong Cheng

*Air Products and Chemicals Inc., 7201 Hamilton Boulevard, Allentown, Pennsylvania 18195-1501, Email: lalgsapci.com

G. S. Lal, G. P. Pez, R. J. Pesaresi, F. M. Prozonic, H. Cheng, J. Org. Chem., 1999, 7048-7054.

DOI: 10.1021/jo990566+

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Abstract

Bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor reagent) is a new deoxofluorinating agent that is much more thermally stable than DAST (C₂H₅)₂NSF₃. It is effective for the conversion of alcohols to alkyl fluorides, aldehydes and ketones to the corresponding gem-difluorides, and carboxylic acids to the trifluoromethyl derivatives with, in some cases, superior performance compared to DAST.

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Fluorination of Thiocarbonyl Compounds with Bis(2-methoxyethyl)aminosulfur Trifluoride (Deoxo-Fluor Reagent):  A Facile Synthesis of gem-Difluorides

G. S. Lal, E. Lobach, A. Evans, J. Org. Chem., 2000, 65, 4830-4832.

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Key Words

Fluoroalkanes, Benzyl Fluorides, Difluoroalkanes, Acyl Fluorides

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ID: J42-Y1999-490