2-DIAZOMETHYL-4-FURANONES. SYNTHESIS AND PROPERTIES

Article abstract of DOI:10.1007/BF00478853

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 acetylenedicarboxylateto a diazomethyl-4-furanone was investigated by means of x-ray diffraction analysis.