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Trifluoromethide as a Strong Base: [CF3] Mediates Dichloromethylation of Nitrones by Proton Abstraction from the Solvent

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posted on 2013-11-15, 00:00 authored by Jean-Bernard Behr, Dani Chavaria, Richard Plantier-Royon
An unprecedented reactivity of CF3-TMS has been revealed, which exploits the basic character of the generated [CF3] capable of delivering dichloromethide from dichloromethane with subsequent transfer to nitrones under smooth conditions. The proton-abstraction pathway was demonstrated through isotopic labeling experiments in CD2Cl2. The same reaction was achieved in acetonitrile with the introduction of a cyanomethyl group onto the nitrones.

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