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

doi:10.1039/A808517J

Paper

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

Published 1999 · G. Lal, G. Pez, Reno Joseph Pesaresi

Chemical Communications

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114

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1

Influential Citations

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Abstract

Bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-FluorTM) is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gem-difluorides 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.

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Study Snapshot

Deoxo-FluorTM is a less sensitive, broader-spectrum alternative to traditional dialkylaminosulfur trifluoride for deoxofluorination of alcohols, aldehydes/ketones, and carboxylic acids.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

Aminosulfur trifluorides: relative thermal stability [1]

Morpholinosulfur trifluoride is the most stable aminosulfur trifluoride, making it a recommended alternative for alcohol fluorination compared to DAST.

Citations

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Sulfone Electrophiles in Cross-Electrophile Coupling: Nickel-Catalyzed Difluoromethylation of Aryl Bromides.

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The Synthesis of Fluorinated Carbohydrates Using Sulfuryl Fluoride as the Deoxyfluorination Reagent.

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Strategies for Nucleophilic C(sp3)-(Radio)Fluorination.

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Synthesis of Highly Reactive Sulfone Iminium Fluorides and Their Use in Deoxyfluorination and Sulfur Fluoride Exchange Chemistry.

SIFs are highly reactive sulfur(VI) molecules that can be synthesized and applied to deoxyfluorination and sulfur fluoride exchange chemistry, providing high yields of fluorinated products in 60 seconds at room temperature.