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

doi:10.1021/jo061450y

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 journal › Article › peer-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 language	English
Pages (from-to)	8250-8255
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	71
Issue number	21
DOIs	https://doi.org/10.1021/jo061450y
Publication status	Published - 13 Oct 2006

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10.1021/jo061450y

CCDC 630245: Experimental Crystal Structure Determination
Griffith, G. A. (Contributor), Hillier, I. (Contributor), Percy, J. M. (Contributor), Roig, R. (Contributor) & Vincent, M. A. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2007
DOI: 10.5517/ccp4th3, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccp4th3&sid=DataCite
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title = "Quantifying the reactivity of a remarkably long-lived difluorinated enol in acidic methanol via solution kinetics and electronic structure calculations",

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. {\textcopyright} 2006 American Chemical Society.",

author = "Griffith, {Gerry A.} and Hillier, {Ian H.} and Percy, {Jonathan M.} and Ricard Roig and Vincent, {Mark A.}",

year = "2006",

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journal = "Journal of Organic Chemistry",

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TY - JOUR

T1 - Quantifying the reactivity of a remarkably long-lived difluorinated enol in acidic methanol via solution kinetics and electronic structure calculations

AU - Griffith, Gerry A.

AU - Hillier, Ian H.

AU - Percy, Jonathan M.

AU - Roig, Ricard

AU - Vincent, Mark A.

PY - 2006/10/13

Y1 - 2006/10/13

N2 - 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.

AB - 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.

U2 - 10.1021/jo061450y

DO - 10.1021/jo061450y

M3 - Article

SN - 0022-3263

VL - 71

SP - 8250

EP - 8255

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

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

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CCDC 630245: Experimental Crystal Structure Determination

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