Rearrangement of penicillins to anhydropenicillins

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Abstract
Anhydropenicillins are derived from penicillins by the removal of a molecule of water from the nucleus with concomitant rearrangement of the thiazolidine ring to an α,β-unsaturated-γ-thiolactone. Conditions are described for the preparation of the acid chlorides of penicillins; these compounds rearrange to anhydropenicillins upon treatment with a tertiary amine. Other less effective ways of performing the rearrangement are also given. The anhydropenicillins show infrared absorption at 5.5, 5.9, 6.0, and 6.1 μ, ultraviolet absorption near 270 mμ (ε = 12 000), and they possess extraordinary chemical stability. Possible reasons for these properties are discussed.

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