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Report | Regular issue | Vol 23, No. 2, 1985, pp.317-323
Published online, 1st January, 1970
DOI: 10.3987/R-1985-02-0317
Debenzylation of N-Benzyl-β-lactams by Use of Anodic Oxidation

Miwako Mori and Yoshio Ban*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

Abstract

Anodic oxidation of N-benzyl-3-methylene-β-lactam 1a followed by hydrolysis with TsOH in 2-butanone gave 3-methylene-β-lactam 4a. To examine the effect of the substituents on the aromatic ring of N-benzyl group for the anodic oxidation, N-p-carbomethoxy, N-p-methyl and N-p-methoxybenzyl-3-methylene-β-lactams were electrolyzed under the same conditions. N-p-Methyl and N-p-methoxybenzyl-β-lactams gave only the exo-methoxylated compounds.