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

    Research output: Contribution to journalArticlepeer-review

    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. © 2006 American Chemical Society.
    Original languageEnglish
    Pages (from-to)8250-8255
    Number of pages5
    JournalJournal of Organic Chemistry
    Volume71
    Issue number21
    DOIs
    Publication statusPublished - 13 Oct 2006

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