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Issue 0, 1973
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Valence-bond isomer chemistry. Part IV. The valence-bond isomers of pentakis(pentafluoroethyl)pyridine

Abstract

Reaction of pentafluoropyridine with tetrafluoroethylene and caesium fluoride in dimethylformamide produces, inter alia, perfluoro-4-ethyl-, -2,4-diethyl-, -2,4,5-triethyl-, -2,3,4,6-tetraethyl-, and -pentaethyl-pyridines. In perfluoro-n-pentane solution, the last compound is isomerized by u.v. light to pentakis(pentafluoroethyl)-1-azabicyclo[2,2,0]hexa-2,5-diene, which in turn forms the corresponding 1-azatetracyclo[2,2,0,02,6,03,5]hexane. These valence-bond isomers show substantial thermal resistance to rearrangement; in hexafluorobenzene solution, the half-life at 170 °C of the hexadiene is 104 h and that of the hexane is 1·1 h.

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Article type: Paper
DOI: 10.1039/P19730001542
Citation: J. Chem. Soc., Perkin Trans. 1, 1973,0, 1542-1545
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    Valence-bond isomer chemistry. Part IV. The valence-bond isomers of pentakis(pentafluoroethyl)pyridine

    M. G. Barlow, R. N. Haszeldine and J. G. Dingwall, J. Chem. Soc., Perkin Trans. 1, 1973, 0, 1542
    DOI: 10.1039/P19730001542

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