jo402028r_si_001.pdf (753.26 kB)
Trifluoromethide as a Strong Base: [CF3–] Mediates Dichloromethylation of Nitrones by Proton Abstraction from the Solvent
journal contribution
posted on 2013-11-15, 00:00 authored by Jean-Bernard Behr, Dani Chavaria, Richard Plantier-RoyonAn 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.