On the anomalous behaviour of certain 1-(4-methoxyphenyl)azetidin-2-ones towards cerium(IV) ammonium nitrate (CAN). Structure-reactivity studies

On treatment with CAN, acetylthiazolidinylazetidin-2-one 12 undergoes ring transformation to afford compound 22, similarly to azetidin-2-ones 2a and 2b studied earlier (all with like configurations at C-4 and C-2′). In contrast, acetylthiazolidinylazetidin-2-one 11 is N-demethoxyphenylated under the...

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Bibliographic Details
Published inTetrahedron Vol. 52; no. 3; pp. 771 - 782
Main Authors Sápi, Attila, Bertha, Ferenc, Fetter, József, Kajtár-Peredy, Mária, Keserű, György M, Lempert, Károly
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.01.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DERIVATIVES
N-DEARYLATION
2-AZETIDINONES
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Summary:On treatment with CAN, acetylthiazolidinylazetidin-2-one 12 undergoes ring transformation to afford compound 22, similarly to azetidin-2-ones 2a and 2b studied earlier (all with like configurations at C-4 and C-2′). In contrast, acetylthiazolidinylazetidin-2-one 11 is N-demethoxyphenylated under the same conditions, similarly to azetidin-2-ones 1a and 1b 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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(95)01036-X