α-Oxocarbene-Oxirene Isomerization: Photolysis of [1-13C]-2-Diazo-1-phenyl-1-propanone and [2-13C]-1-Diazo-1-phenyl-2-propanone

Authors

  • Priv.-Doz. Dr. Klaus-Peter Zeller

    Corresponding author
    1. Institut für Organische Chemie der Universität, Auf der Morgenstelle 18, D-7400 Tübingen 1 (Germany)
    • Institut für Organische Chemie der Universität, Auf der Morgenstelle 18, D-7400 Tübingen 1 (Germany)
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  • This work was supported by the Deutsche Forschungsgemeinschaft.

Abstract

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Equilibration between two isomeric oxocarbenes has now been studied quantitatively for the first time starting from both13C-labeled diazoketones. Oxocarbene (1) reacts preferentially via the oxirene (2) to form (3), while (3) undergoes mainly direct Wolff rearrangement to the ketene.

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