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An oxidation reaction of hydroxyhomosumanene on silica gel providing homosumanene ortho‐quinone and its synthetic application for azaacene‐fused homosumanenes is described. Hydroxyhomosumanene is photochemically oxidized by air, when it is coated on silica gel; this aerobic oxidation proceeds faster than that of planar analogues. The difference of such reactivity was attributed to the unusual keto‐enol...
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