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Mechanism of organic reaction showing electron movement

Submitted by kika09 on Thu, 11/08/2007 - 20:28

Tetraphennylcyclopentadiene reacts with diphenylacetylene to give hexaphenylbenzene and CO. Draw a detailed arrow pushing mechanism for this reaction

  Where is your oxygen source for the production of carbon monoxide? I think, your reactant should be a 1-keto-2,3,4,5-tetraphenylcyclopentadiene rather than a tetraphenylcyclopentadiene. Using the ketone, a Diels-Alder type reaction would create a bicyclic [2,2,1] compound, with the keto group on the single bridging carbon. Then, another Diels-Alder mechanism would take place to produce hexaphenylbenzene and carbon monoxide.