Quantifying the Reactivity of a Remarkably Long-Lived Difluorinated Enol in Acidic Methanol via Solution Kinetics and Electronic Structure Calculations

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• 作者：Gerry A. Griffith ; Ian H. Hillier ; Jonathan M. Percy ; Ricard Roig ; Mark A. Vincent
• 刊名：Journal of Organic Chemistry
• 出版年：2006
• 出版时间：October 13, 2006
• 年：2006
• 卷：71
• 期：21
• 页码：8250 - 8255
• 全文大小：161K
• 年卷期：v.71,no.21(October 13, 2006)
• ISSN：1520-6904

文摘

ABLE>als/joceah/71/i21/figures/jo061450yn00001.gif" ALIGN="left" HSPACE=5>A simple enol acetal underwent rapid cleavage in acidic solution to generate a difluorinated enol, whichwas 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 differencesin protonation transition state timing between the fluorinated and nonfluorinated enols.