The mechanism of the alkylation of isoxazolidin-3-one

In solvents of different polarities, the lactam-lactim tautomeric equilibrium of isoxazoli-din-3-one is strongly displaced in the direction of the lactam. The lactim form cannot be detected. It has been concluded that there is no connection between the dual chemical behavior of isoxazolidin-3-one and its potassium salt in the alkylation reaction with the equilibrium isomerization of these compounds. It has been shown that the mechanism of alkylation is connected with the structure of the lactam anion. Evidence is given in favor of a mesomeric structure of the anion with the main charge on the nitrogen at which substitution chiefly takes place.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 898–901, July, 1973.