Rearrangements of penicillin sulphoxides

Abstract
Isomerisation of a penicillin G (R)-sulphoxide into the corresponding (S)-isomer proceeds by a sulphenic acid intermediate which has been trapped by deuterium incorporation; in the rearrangement of the t-butylamides of the (S)-sulphoxide of penicillin G only cepham and penam derivatives are isolated and no cephem products are formed.

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