Abstract
Penicillanate (S)-S-oxides reacted with ethyl N-chloro-N-sodiocarbamate to give 6α-ethoxyformamido-derivatives together with the corresponding 6-epi-penicillanate, an intermediate in the formation of the former product. The (R)-S-oxides reacted with N-chloro-N-sodiocarbamate to give 6α-alkoxyformamido-derivatives, together with 6,6-bis(alkoxyformamido)penam (R)-S-oxides, which were further transformed into cephalosporanates. Mechanisms for these substitution reactions are discussed.
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