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

Attila Sápi, Ferenc Bertha, J. Fetter, M. Kajtár-Peredy, György M. Keseru, Károly Lempert

Research output: Contribution to journalArticle

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Abstract

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-demethoxy-phenylated 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.

Original languageEnglish
Pages (from-to)771-782
Number of pages12
JournalTetrahedron
Volume52
Issue number3
DOIs
Publication statusPublished - Jan 15 1996

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cerium(IV) ammonium nitrate

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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On the anomalous behaviour of certain 1-(4-methoxyphenyl)azetidin-2-ones towards cerium(IV) ammonium nitrate (CAN). Structure-reactivity studies. / Sápi, Attila; Bertha, Ferenc; Fetter, J.; Kajtár-Peredy, M.; Keseru, György M.; Lempert, Károly.

In: Tetrahedron, Vol. 52, No. 3, 15.01.1996, p. 771-782.

Research output: Contribution to journalArticle

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AU - Lempert, Károly

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AB - 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-demethoxy-phenylated 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.

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