Attempts to introduce oxygenated substituents into the allylic methyl groups of derivatives of (3R,4R)-3-amino-1-(1-carboxy-2-methylprop-1-enyl)-4-mercaptoazetidin-2-one failed. Instead lead tetra-acetate and certain other oxidants attacked the sulphur atom and the adjacent carbon atoms, whereas osmium tetraoxide or potassium permanganate removed the complete substituent from the β-lactam nitrogen atom.
E. G. Brain, A. J. Eglington, J. H. C. Nayler, M. J. Pearson and R. Southgate, J. Chem. Soc., Perkin Trans. 1, 1976, 447 DOI: 10.1039/P19760000447
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