Ketones react with dimethylsulfonium methylide to yield epoxides. The reaction occurs by an initial nucleophilic addition, followed by an SN2 reaction. Propose a mechanism.
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Step 1
The negatively charged carbon in the methylide attacks the electrophilic carbonyl carbon of the ketone. This results in the formation of a tetrahedral intermediate, where the carbonyl oxygen now carries a negative charge. Show more…
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