ON THE ANOMALOUS BEHAVIOR OF CERTAIN 1-(4-METHOXYPHENYL)AZETIDIN-2-ONES TOWARDS CERIUM(IV) AMMONIUM-NITRATE (CAN) - STRUCTURE-REACTIVITY STUDIES

Authors
SAPI A BERTHA F FETTER J KAJTARPEREDY M KESERU GM LEMPERT K
Citation
A. Sapi et al., ON THE ANOMALOUS BEHAVIOR OF CERTAIN 1-(4-METHOXYPHENYL)AZETIDIN-2-ONES TOWARDS CERIUM(IV) AMMONIUM-NITRATE (CAN) - STRUCTURE-REACTIVITY STUDIES, Tetrahedron, 52(3), 1996, pp. 771-782
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
3
Year of publication
1996
Pages
771 - 782
Database
ISI
SICI code
0040-4020(1996)52:3<771:OTABOC>2.0.ZU;2-L
Abstract
On treatment with CAN, acetylthiazolidinylazetidin-2-one 12 undergoes ring transformation to afford compound 22, similarly to azetidin-2-one s 2a and Ib studied earlier (all with like configurations at C-4 and C -2'). In contrast, acetylthiazolidinylazetidin-2-one 11 is N-demethoxy phenylated under the same conditions, similarly to azetidin-2-ones la and Ib studied earlier (all with unlike configurations at C-4 and C-2' ). Both epimers, with like as well as unlike configurations at C-4 and C-2', of acetyloxazolidinyl derivative 7 are N-demethoxyphenylated by CAN. These observations support the mechanism, suggested earlier for the CAN induced novel ring transformation reaction.