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Cheletropic extrusion

2 real reactions from the literature, on cyclopentadienones. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Cheletropic extrusion: 2,3,4,5-tetraphenyl-2,4-cyclopentadien-1-one (a cyclopentadienone) and diphenylacetylene (an internal alkyne) with Δ; (–CO) gives hexaphenylbenzene (the aromatized product).

  2. Cheletropic extrusion: 2-phenyliodoniobenzoate (a diaryliodonium salt) and 2,3,4,5-tetraphenyl-2,4-cyclopentadien-1-one (a cyclopentadienone) with diethyl benzene, Δ; (–CO, –CO2) gives 1,2,3,4-tetraphenylnaphthalene (the aromatized product).