Quantifying the reactivity of a remarkably long-lived difluorinated enol in acidic methanol via solution kinetics and electronic structure calculations

Gerry A. Griffith, Ian H. Hillier, Jonathan M. Percy, Ricard Roig, Mark A. Vincent

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Abstract

A simple enol acetal underwent rapid cleavage in acidic solution to generate a difluorinated enol, which was sufficiently long-lived to be characterized by 2D NMR in a protic solvent at ambient temperature. Density functional theory calculations on a model reaction suggest that there are significant differences in protonation transition state timing between the fluorinated and nonfluorinated enols.
Original languageEnglish
Pages (from-to)8250-8255
Number of pages6
JournalJournal of Organic Chemistry
Volume71
Issue number21
DOIs
Publication statusPublished - 22 Sep 2006

Keywords

  • difluorinated enol
  • 2D NMR
  • fluorinated enol
  • organic chemistry
  • reactivity
  • long-lived difluorinated enol

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