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).
|Number of pages||5|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|Publication status||Published - 1975|