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Communication | Regular issue | Vol 26, No. 4, 1987, pp.885-894
Published online, 1st January, 1970
DOI: 10.3987/R-1987-04-0885
Chemistry of Penicillin Diazoketones. Part II. from Beta-lactam to Beta-lactone

Hans Ludescher, Ching-Pong Mak, Gerhard Schulz, and Hans Fliri

*Sandoz Forschungsinstitut, 1235 Wien, Brunnerstraße 59, Austria


Carbenes formed by transition metal catalyzed decomposition of penicillin-derived diazoketones can undergo different reaction pathways, depending on the presence or absence of the gem-dimethyl group. In the presence of the gem-dimethyl group products are formed via a sulfur ylide intermediate. Bis-nor derivatives undergo Wolff-rearrangement into ketenes which react further to give isopenams. If an hydroxyethyl substituent is present at C-6 of the starting material the original β-lactam is converted into a β-lactone.