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Communication | Regular issue | Vol 16, No. 9, 1981, pp.1487-1490
Published online, 1st January, 1970
DOI: 10.3987/R-1981-09-1487
New Synthetic Applications of 4-Acetoxyazetidin-2-one: Carboxylate and Nitrogen Nucleophile Displacements

Malcolm M. Campbell* and V. John Jasys

*School of Chemistry, University of Bath, Bath, Avon. BA2 7AY, U.K.


Reaction conditions for displacement of the acetate group in 4-acetoxyazetidin-2- one by carboxylate and nitrogen nucleophiles have been studied, giving firstly, a 4-malonyloxyazetidin-2-one from which was synthesized the clavulanic acid degradation product benzyl 3,7-dioxo-4-oxa-1-aza[3.2.0.]bicycloheptan-7-one 2-carboxylate, and secondly, new routes to 4-aza substituted azetidin-2-ones.