Activation of weak nucleophiles: Polyfluorocarbamates from polyfluoroalcohols via a fast radical reaction

Marc Soto, Helena Comalrena, Ursula Balduzzi, Gonzalo Guirado, Vega Lloveras, José Vidal-Gancedo, Rosa María Sebastián, Jordi Marquet

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1 Citation (Scopus)

Abstract

A new fast radical mechanism has been observed for the reaction of polyfluorinated alcohols and phenylisocyanate, very sensitive to the change of solvents and the concentration of reactants. The acidity of polyfluoroalcohols seems to be responsible for the observed new reactivity and evidences from kinetic studies, electron paramagnetic resonance, cyclic voltammetry, and photostimulation suggest that polyfluoroalkoxy radical is the key intermediate in the chain. To the best of our knowledge, it is the first time that a radical mechanism is described for the preparation of carbamates. © 2013 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)6310-6313
JournalTetrahedron Letters
Volume54
Issue number47
DOIs
Publication statusPublished - 20 Nov 2013

Keywords

  • Cyclic voltammetry
  • Electron paramagnetic resonance
  • Polyfluorocarbamates
  • Radical chain reaction
  • Single electron transfer

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