4.7 Article

Methyl 2,2-Difluoro-2-(fluorosulfonyl)acetate, a Difluorocarbene Reagent with Reactivity Comparable to That of Trimethylsilyl 2,2-Difluoro-2-(fluorosulfonyl)acetate (TFDA)

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 12, Pages 5461-5464

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo300876z

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Under specific high concentration, high temperature conditions, methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (MDFA) has been found to act as a very efficient source of difluorocarbene, exhibiting carbene reactivity characteristics comparable to those exhibited by trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate (TFDA). For example, in reaction with highly unreactive n-butyl acrylate and using only 2 equiv of MDFA, a yield of 76% of difluorocyclopropane product was obtained after 2 days.

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