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Issue 23, 2018
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Diels–Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control

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Abstract

The tandem [4+2] cycloaddition between hexafluoro-2-butyne and bis-furyl dienes, like difurfuryl ester, at room temperature leads to the kinetically controlled “pincer”-adducts – annulated 4a,8a-bis(trifluoromethyl)hexahydro-1,4:5,8-diepoxynaphthalenes. On the other hand, if these reactions proceed at 140 °C, only the thermodynamically controlled “domino”-adducts – annulated 2,3-bis(trifluoromethyl)hexahydro-1,4:5,8-diepoxynaphthalenes – are formed. Therefore, a very rare and unexpected example of full kinetic and thermodynamic control in the Diels–Alder reaction is reported in this paper.

Graphical abstract: Diels–Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control

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Publication details

The article was received on 09 Dec 2017, accepted on 24 Jan 2018 and first published on 02 Feb 2018


Article type: Communication
DOI: 10.1039/C7CC09466C
Citation: Chem. Commun., 2018,54, 2850-2853
  • Open access: Creative Commons BY-NC license
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    Diels–Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control

    K. K. Borisova, E. V. Nikitina, R. A. Novikov, V. N. Khrustalev, P. V. Dorovatovskii, Y. V. Zubavichus, M. L. Kuznetsov, V. P. Zaytsev, A. V. Varlamov and F. I. Zubkov, Chem. Commun., 2018, 54, 2850
    DOI: 10.1039/C7CC09466C

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