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

Griffith, Gerry A. and Hillier, Ian H. and Percy, Jonathan M. and Roig, Ricard and Vincent, Mark A. (2006) Quantifying the reactivity of a remarkably long-lived difluorinated enol in acidic methanol via solution kinetics and electronic structure calculations. Journal of Organic Chemistry, 71 (21). pp. 8250-8255. ISSN 0022-3263 (https://doi.org/10.1021/jo061450y)

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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.

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• Item metadata

  Item type:	Article
  ID code:	10082
  Dates:	Date Event 22 September 2006 Published 12 July 2006 Accepted
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Strathprints Administrator
  Date deposited:	16 Nov 2011 11:07
  Last modified:	25 Apr 2024 00:18
  URI:	https://strathprints.strath.ac.uk/id/eprint/10082