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Issue 4, 2012
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Atropisomerism of a monosubstituted perfluoro[2.2]paracyclophane. A combined synthetic, kinetic, spectroscopic and computational study

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Abstract

The product of SNAr addition of the enolate of ethyl acetoacetate to perfluoro[2.2]para-cyclophane exists entirely as its enol tautomer 5. This enol exhibits two NMR signals for its enolic proton, and these signals were shown to derive from the presence of two, equal energy conformations that were observable as distinct, stable conformations at room temperature, but which when heated, interconverted with an energy barrier of 23.5 kcal mol−1. These atropisomers were characterized by NMR, with details of this analysis being provided. Computational work corroborated the NMR conclusions, and provided additional insight into all structural, thermodynamic and kinetic results. Enol product 5 was cyclized, under basic conditions, to form a benzofuran product 6. Its structure was confirmed by NMR, with further structural and mechanistic insights being provided by calculations.

Graphical abstract: Atropisomerism of a monosubstituted perfluoro[2.2]paracyclophane. A combined synthetic, kinetic, spectroscopic and computational study

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Publication details

The article was received on 12 Jul 2011, accepted on 10 Oct 2011 and first published on 11 Oct 2011


Article type: Paper
DOI: 10.1039/C1OB06157G
Org. Biomol. Chem., 2012,10, 882-889

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    Atropisomerism of a monosubstituted perfluoro[2.2]paracyclophane. A combined synthetic, kinetic, spectroscopic and computational study

    I. Ghiviriga, H. Martinez, C. Kuhn, L. Zhang and W. R. Dolbier, Org. Biomol. Chem., 2012, 10, 882
    DOI: 10.1039/C1OB06157G

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