Abstract
1,5-Bisdiazo-3-alkylpentane-2,4-diones were synthesized by the reaction of alkylmalonic acid chlorides with diazomethane; the products readily undergo intramolecular cyclization at the oxygen atom and one of the diazoacetyl groups under the influence of acidic agents with the formation of 2-diazomethyl-3-alkyl-4-furanones. It is shown that diazomethyl-4-furanones, which are vinylogs of α-diazo ketones, undergo reactions that are characteristic for aliphatic diazo compounds. The structure of the product of 1,3-dipolar cycloaddition of dimethyl acetylenedicarboxylate to a diazomethyl-4-furanone was investigated by means of x-ray diffraction analysis.
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