Chemistry of oxalyl derivatives of methyl ketones. 28. Reaction of carbonyl compounds of adamantane with 5-phenyl-2,3--dihydrofuran-2,3-dione

Abstract

The reaction of substituted methyl 1-adamantyl ketones with an equimolar amount of 5-phenyl-2,3-dihydrofuran-2,3-dione under the conditions of the thermal decarbonylation of the latter leads to the corresponding 2-methyl-2-adamantyl-6-pheny1-1,3-dioxen-4-ones, 6-phenyl-3-benzoyl-2,4-dione, and the starting ketones. The steric and electronic factors that affect the yields of the dioxen-4-ones were examined. α-Hydroxymethyl 1-adamantyl ketones open up the furan ring to give 1-adamantoylmethyl benzoylpyruvate. Data from the IR, PMR, and UV spectra are presented.