Rearrangement of penicillins to anhydropenicillins

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 rearr...

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Bibliographic Details
Published in:Canadian journal of chemistry 1968-08, Vol.46 (15), p.2549-2559
Main Authors: Wolfe, Saul, Godfrey, J. C, Holdrege, C. T, Perron, Y. G
Format: Article
Language:English
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Summary: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 (  = 12 000), and they possess extraordinary chemical stability. Possible reasons for these properties are discussed.
ISSN:0008-4042
1480-3291
DOI:10.1139/v68-417