ANOMALOUS N-METHYLMORPHOLINE N-OXIDE OSMIUM TETROXIDE OXIDATION OF PENICILLINS AND CEPHALOSPORINS/

Authors
TAMAS L SZOKE GN GUNDA TE SZTARICSKAI F
Citation
L. Tamas et al., ANOMALOUS N-METHYLMORPHOLINE N-OXIDE OSMIUM TETROXIDE OXIDATION OF PENICILLINS AND CEPHALOSPORINS/, ACH, models in chemistry, 135(1-2), 1998, pp. 207-212
Citations number
25
Categorie Soggetti
Chemistry
Journal title
ACH, models in chemistry → ACNP
ISSN journal
12178969
Volume
135
Issue
1-2
Year of publication
1998
Pages
207 - 212
Database
ISI
SICI code
1217-8969(1998)135:1-2<207:ANNOTO>2.0.ZU;2-8
Abstract
The penicillin and cephalosporin sulfides and beta-sulfoxides behave s uprisingly disparately when subjected to oxidation with N-methylmorpho line N-oxide and osmium tetroxide: while penicillins are inert to this oxidation procedure, their sulfoxides are cleanly converted to the su lfones, In the case of cephalosporins only Delta(3) --> Delta(2) isome rization was observed. Cephem sulfoxides failed to react or yielded on ly degradation products, only the 3-exomethylene-cepham derivative yie lded the corresponding 3-hydroxy-cephem sulfone.