Synthesis of Polysubstituted Dioxoles from the Cycloaddition of Diazo Dicarbonyl Compounds to Aldehydes and Ketones under Copper(II) Catalysis

Article abstract of DOI:10.1021/jo00219a005

The copper(II) chelate catalyzed addition of compounds 2-diazo-3-oxobutyrate (3) and 3-diazo-2,4-pentanedione (5) in the presence of aldehydes and ketones in refluxing aromatic solvents proceeds smoothly with the exlusive formation of dioxole derivatives.The yield of 1:1 adducts depends strongly on the nature of the copper ligands and relative concentration of catalyst employed.Dioxoles are the only volatile materials present within a 2percent detection limit. The general character of this novel cycloaddition is illustrated with the reaction of 3 and 5 with four aldehydes and nine ketone substrates.