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.
D. H. R. Barton, F. Comer, D. G. T. Greig, G. Lucente, P. G. Sammes and W. G. E. Underwood, J. Chem. Soc. D, 1970, 1059 DOI: 10.1039/C29700001059
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