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    Université de Fribourg

    The bisketene radical cation and its formation by oxidative ring-Opening of cyclobutenedione

    Piech, Krzysztof ; Bally, Thomas ; Allen, Annette D. ; Tidwell, Thomas T.

    In: The Journal of Organic Chemistry, 2013, vol. 78, no. 7, p. 2908–2913

    Parent cyclobutenedione 1 was photolyzed and ionized in an Ar matrix at 10K. The bisketene 2 that results in both cases (in the form of its radical cation after ionization) was characterized by its IR spectrum and by high-level quantum chemical calculations. Experiment and theory show that the neutral bisketene has only a single conformation where the two ketene moieties are nearly perpendicular,...