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Epoxidation
Epoxidation reactions:
- occurs in a single, concerted step
- produces a three membered oxygen-containing ring (the epoxide!)
- the addition of the three-membered ring is syn (i.e. on the same side) for the stereochemical outcome
Wize Concept
There are many peroxyacids that can be used for this reaction, but the most common is meta-chloroperoxybenzoic acid (m-CPBA, shown below).
Steps of a epoxidation:
- a concerted (single-step) reaction of the peroxyacid across the alkene to make the epoxide
Mechanism:
Watch Out!
These reactions are stereospecific which means they maintain the geometry of the reagent. This means that cis double bonds stay cis and trans double bonds stay trans.
Example: predict the product of the following epoxidation reactions.
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Example: Epoxidation
Provide the product(s) of the following epoxidation reactions.
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Example: Epoxides as Electrophiles
Draw mechaisms to explain the products of the following reactions of epoxides as electrophiles.
