Oxacyclopropane Epoxide Synthesis Epoxidation by Peroxycarboxylic Acids

OXACYCLOPROPANE (EPOXIDE) SYNTHESIS EPOXIDATION BY PEROXYCARBOXYLIC ACIDS 

This section describes how an electrophilic oxidizing agent is capable of introducing a single oxygen atom to connect to both carbons of a double bond. This produces oxacyclo-propanes, which may, in turn, be converted into vicinal anti diols. Sections 12-11 and 12-12 

Peroxycarboxylic acids deliver oxygen atoms to double bonds 

The transfer of oxygen is stereospeciflcally syn, the stereochemistry of the starting alkene being retained in the product. For example, trans-l-hateae, gives trans-2,3-dimethyloxacyclopropane conversely, the di-2-butene yields di-2,3-dimethyloxa-cyclopropane. 

Outline a short synthesis of tra s-2-methylcyclohexanol from cyclohexene. (Hint Review the reactions of oxacyclopropanes in Section 9-9.) 

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