β-Elimination as a general process in penicillin chemistry. The stereochemistry and mechanism of Raney nickel desulphurisation of penicillin G and penicillin V

Abstract

The conversions of penicillin G and penicillin V into their dethio-derivatives with deuteriated Raney nickel proceed with retention of configuration at C-5 and with extensive incorporation of deuterium on the gem-dimethyl groups: a β-elimination mechanism is suggested to explain these results and the generality of β-elimination in penicillin chemistry is noted.