The Reaction of Carbon Suboxide with Alicyclic Diketones and with Phenols. Formation and Structure of Pyrone Derivatives

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Abstract
The reactions of carbon suboxide with alicyclic diketones and with phenols were found to give various pyrone derivatives. From the reaction of 5,5-dimethyl-1,3-cyclohexanedione, 4-hydroxy-7,7-dimethyl-5,6,7,8-tetrahydro-2H-benzo[b]pyran-2,5-dione (II) was produced in the presence of a sulfuric acid catalyst. However, the reaction with 1,2-cyclohexanedione gave the malonic acid diester (III), and the formation of corresponding pyrone was not observed. The reaction of phenols with carbon suboxide gave only esters of malonic acid in the presence of the sulfuric acid catalyst, whereas cyclization to coumarin derivatives occurred on the presence of aluminum trichloride, in addition to the formation of the esters. The structure of the pyrone derivatives and the possible reaction mechanism were discussed.

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