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Payne Rearrangement

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Casual Chemistry

Mechanism for the isomerisation of epoxy alcohols to the terminal epoxide. It is likely that the initial epoxide was generated by oxidation of an allylic alcohol perhaps by asymmetric catalysis using a Sharpless Asymmetric Epoxidation reaction. The terminal epoxide is favoured as it has less steric strain from eclipsing interactions.

posted by kolesomsa