Abstract
A formal insertion of two aryne moieties into the carbon-oxygen double bond of cyclopropenone has been realized. Spirocyclic xanthene-cyclopropene scaffolds were obtained. Mechanistically, a sequence of a formal [2 + 2]-cycloaddition followed by electrocyclic ring opening and a terminating [4 + 2]-type cycloaddition is postulated. The use of an electron-rich aryne precursor led to ring cleavage of the cyclopropene to afford an unprecedented xanthylium salt.
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