Conversion of secopenicillanic acid derivatives into β-lactam sulphimides and oxazolines

Malcolm M Campbell, Graham Johnson

Research output: Contribution to journalArticle

Abstract

4-(Methylthio)azetidin-2-ones when treated with chloramine T gave in each case a single sulphimide enantiomer, together with both possible sulphoxides. The sulphimides were readily converted by heating, or by attempted oxidation or reduction, into ß-lactam fused oxazolines. The 4-methylthio-3- (triphenylmethylamino)azetidin-2-one derivative did not undergo comparable reaction with chloramine T.

Original languageEnglish
Pages (from-to)1077-1081
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number12
Publication statusPublished - 1975

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Lactams
Derivatives
Acids
Enantiomers
Heating
Oxidation
chloramine-T

Cite this

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abstract = "4-(Methylthio)azetidin-2-ones when treated with chloramine T gave in each case a single sulphimide enantiomer, together with both possible sulphoxides. The sulphimides were readily converted by heating, or by attempted oxidation or reduction, into {\ss}-lactam fused oxazolines. The 4-methylthio-3- (triphenylmethylamino)azetidin-2-one derivative did not undergo comparable reaction with chloramine T.",
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Conversion of secopenicillanic acid derivatives into β-lactam sulphimides and oxazolines. / Campbell, Malcolm M; Johnson, Graham.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 12, 1975, p. 1077-1081.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Conversion of secopenicillanic acid derivatives into β-lactam sulphimides and oxazolines

AU - Campbell, Malcolm M

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AB - 4-(Methylthio)azetidin-2-ones when treated with chloramine T gave in each case a single sulphimide enantiomer, together with both possible sulphoxides. The sulphimides were readily converted by heating, or by attempted oxidation or reduction, into ß-lactam fused oxazolines. The 4-methylthio-3- (triphenylmethylamino)azetidin-2-one derivative did not undergo comparable reaction with chloramine T.

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