1-Acyloxyaziridine-2,2-dicarboxylic acid esters

The reaction of diazomethane and O-acylisonitrosomalonates gave ²-1,2,3-triazoline-5,5-dicarboxylic acid esters, the rates of formation and thermal stabilities of which are determined by the character of ths substituent attached to the oxygen atom. Thermolysis of the triazolines leads to mixtures of 1-acyloxyaziridine-2,2-dicarboxylic acid esters and isomeric dialkyl O-acylisonitrososuccinates; acidolysis with BF₃·Et₂O makes it possible to obtain exclusively aziridines. The acidic decompositions of dimethyl 4-methyl-²-1,2,3-triazoline-5,5-dicarboxylate, which was obtained from the reaction of diazoethane and dimethyl O-tosylisonitrosomalonate, leads to dimethyl -tosyloxyamino--vinylmalonate. A dependence of the spin-spin coupling constants (SSCC) of the protons of the aziridine ring on the electronegativities of the substituents attached to the oxygen atom was observed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 338–342, March, 1984.