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Paper | Regular issue | Vol 29, No. 4, 1989, pp.719-727
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4838
The Behaviour of 4-Benzoyl-2-azetidinones with Bases. Regioselectivity in Their Alkylation Reactions

Benito Alcaide, Gema Dominguez, Angel Martín-Domenech, Inmaculade Martín, Carlos Cativiela, José A. Mayoral, and Joaquín Plumet*

*Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Extremadura, Avenida de Elvas s/n, 06071-Badajoz, Spain

Abstract

4-Benzoyl-2-azetidinones react with alkyl halides in the presence of bases in a regioselective fashion depending on the substitution pattern in the β-lactam ring and on the alkylating agent. In this way, different kinds of products derived from C- and O-alkylation of 4-benzoyl-β-lactams, 10, 11, 14, and 16, as well as products derived from ring expansion of the β-lactam moiety and subsequent O-alkylation, 15, have been obtained. In addition, the reaction course for the isomerization of cis-4-benzoyl-2-azetidinones 1 has been elucidated on the basis of experimental data and MNDO calculations.