Reactions of sulphur nucleophiles with activated derivatives of clavulanic acid

Abstract
Allylic halides (e.g.2), prepared from 4-nitrobenzyl clavulanate, react with salts of thiocarboxylic, thiocarbamic, and sulphinic acids to give thioesters, thiocarbamates, and sulphones; dehydrohalogenation of the halides affords the diene (4), from which sulphur derivatives may also be prepared via a stereospecific 1,4-addition reaction.

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