A new synthetic route to 2-azetidinones. Ring contraction of 4-azido-2-pyrrolinones to 3-cyano-2-azetidinones

HW Moore, L Hernandez Jr, DM Kunert…

Index: Moore,H.W.; Hernandez,L.; Kunert,D.M. Journal of the American Chemical Society, 1981 , vol. 103, p. 1769

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Citation Number: 24

Abstract

Abstract: Thermolysis or photolysis of 4-azido-2-pyrrolinones results in their ring contraction to 3-cyano-2-azetidinones. The mechanism of this rearrangement is discussed, and evidence is presented to establish zwitterionic intermediates as the penultimate precursors to the 2-azetidinones.