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Article

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

J. Org. Chem., 1999, 64 (19), pp 7048–7054

DOI: 10.1021/jo990566+

Publication Date (Web): August 21, 1999

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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.

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Published In Issue September 17, 1999
Received March 30, 1999

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Article

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

Abstract

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History

Recommend & Share

Related Content

New fluorinating reagents. Dialkylaminosulfur fluoridesNew fluorinating reagents. Dialkylaminosulfur fluorides

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

[Bis(2-methoxyethyl)amino]sulfur Trifluoride, the Deoxo-Fluor Reagent: Application toward One-Flask Transformations of Carboxylic Acids to Amides

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