Octahydro-1,2,3:4,5,6-dimethenopentalene-2-carbonitrile, the First Derivative of a Yet-Unknown (CH)10 Hydrocarbon


  • This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. We thank CHEMETALL GmbH, Union Rheinische Braunkohlen Kraftstoff AG, and Hoechst AG for donating chemicals.


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Two proximate bicyclobutane units are contained in the new hexacycle 3. Their arrangement facilitates a transannular reaction in the radical addition of thiophenol to give the cage compound 4. Starting from benzvalene (1), the route to 3 comprises only five steps: the first (12) is a Pauson-Khand reaction.