Nucleophilic and solvolytic ring opening of epoxides

SECTION 10.2. ADDITION OF OXYGEN AT CARBON-CARBON DOUBLE BONDS 

Enol acetates form epoxides which can rearrange to a-acetoxy ketones  

The stereochemistry of the rearrangement of the acetoxy epoxides involves inversion at the carbon to which the acetoxy group migrates.The reaction probably proceeds through a cyclic transition state. 

A more synthetically useful version of this reaction involves epoxidation of enol trimethylsilyl ethers of ketones. The methods for synthesis of these compounds were discussed in Section 1.2. Epoxidation of the silyl enol ethers followed by aqueous workup gives a-hydroxy ketones and a-hydroxy aldehydes.The oxidation 

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Scheme 12.15. Nucleophilic and Solvolytic Ring Opening of Epoxides...

Nucleophilic Substitution Solvolytic and Elimination Reactions Ring-opening of Epoxides Esters, Ethers, and Related Derivatives of Alcohols Oxidation Reduction Miscellaneous... 

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