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Pure Appl. Chem., 2005, Vol. 77, No. 12, pp. 2061-2071

http://dx.doi.org/10.1351/pac200577122061

New reactions of functionalized β-lactams

Willem Van Brabandt, Yves Dejaegher and Norbert De Kimpe

Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium

Abstract: An easy synthesis of 4-(1- and 2-haloalkyl)azetidin-2-ones by a [2+2] cycloadditon protocol is described. Starting from these functionalized β-lactams, new pathways toward bicyclic β-lactams were developed via intramolecular nucleophilic substitutions and radical cyclizations. 4-(1- and 2-Haloalkyl)azetidin-2-ones also proved to be very useful starting products in the synthesis of various highly substituted aziridines, azetidines, and alkenoates.