Epimerisation of penicillanic acid derivatives and their rearrangement to 1,4-thiazepines: evidence for an E1cB mechanism
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society D: Chemical Communications
- No. 9,p. 450-452
- https://doi.org/10.1039/c29710000450
Abstract
A common enolate-like intermediate is implicated in the weak base-catalysed conversion of methyl 6β-phthalimidohomopenicillanate into methyl 6α-phthal-imidohomopenicillanate and methyl 2,3,4,7-tetrahydro-2,2-dimethyl-7-oxo-6-phthalimido-1,4-thiazepine-3(S)-acetate.Keywords
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