Depto. Química Orgánica

ALKENE EPOXIDATION

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15/07/2017
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Oxidation of olefins with peroxyacids leads to epoxides in a direct, easy and clean manner.
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The most utilized peroxycarboxylic acids are:
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The reaction is very selective:
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The peroxyacid is attacked by the olefin bearing the highest electronic density, i.e. by the most substituted one.
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Olefin epoxidation combined with the aperture of the resulting epoxide with water in acidic medium, is an excellent method to get anti-alcohols:
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The trans stereochemistry of the starting olefin makes the reaction produce the meso form.
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In turn, the cis olefin leads to a racemic mixture.