CHEMISTRY OF PENICILLIN DIAZOKETONES .2. FROM BETA-LACTAM TO BETA-LACTONE

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-n...

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Bibliographic Details
Published inHeterocycles Vol. 26; no. 4; pp. 885 - 894
Main Authors LUDESCHER, H, MAK, CP, SCHULZ, G, FLIRI, H
Format Journal Article
LanguageEnglish
Published Tokyo Japan Inst Heterocyclic Chemistry 01.04.1987
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary: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 hydroxylethyl substituent is present at C-6 of the starting material the original .beta.-lactam is converted into a .beta.-lactone.
ISSN:0385-5414
1881-0942
DOI:10.3987/R-1987-04-0885