Photolysis of 5-diazo-2,2-dimethyl-4,6-dioxo-1,3-dioxane (diazoisopropylidenemalonic acid)

The principal pathway in the photochemical ( > 210 nm) transformation of 5-diazo-2,2-dimethyl-4,6-dioxo-1,3-dioxane in an aqueous medium (or in methanol) is splitting out of nitrogen and the Wolff rearrangement to give the stable 2,2-dimethyl-5-oxo-1,3-dioxolane-4-carboxylic acid (or its methyl ester), which undergoes decarboxylation only at temperatures above 150 ° C, whereas it undergoes hydrolysis to a hydroxymalonic acid in the presence of trifluoroacetic acid.Communication 6 from the series Chemistry of diazo dicarbonyl compounds. See 1] for Communication 5.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 321–325, March, 1985.