Transformations of penicillins: Reactions with chloramine T

Malcolm M Campbell, Graham Johnson, A. F. Cameron, I. R. Cameron

Research output: Contribution to journalArticle

Abstract

Reaction of chloramine T trihydrate with certain 6ß- amidopenicillanates affords ß-lactam-fused thiadiazine S-imides. The structure of one S-imide was established by X-ray crystallography and those of the others were deduced by spectroscopic comparison. Penicillanates lacking a secondary amide group at C-6 did not undergo comparable reaction. The ß-lactam-fused heterocyclic S-imides were particularly stable towards a series of reactants, including oxidising and reducing reagents. Trichloroethyl 6ß-phenylacetamidopenicillanate was significantly different in its reactivity towards chloramine T, affording ß-lactam-fused oxazolines and a monocyclic chloroazetidinone. A by-product in these reactions was identified as NN'-thiobis(toluene-p-sulphonamide).

Original languageEnglish
Pages (from-to)1208-1212
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number13
Publication statusPublished - 1975

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    Campbell, M. M., Johnson, G., Cameron, A. F., & Cameron, I. R. (1975). Transformations of penicillins: Reactions with chloramine T. Journal of the Chemical Society, Perkin Transactions 1, (13), 1208-1212.