Alkyl Halides to Dialkyl Ethers

When primary alkyl phenyl tellurium or secondary alkyl phenyl tellurium compounds in methanol were treated with an excess of 3-chloroperoxybenzoic acid at 20°, the phenyltelluro group was eliminated and replaced by a methoxy group. This reaction, which converts alkyl halides used in the synthesis of alkyl phenyl telluriums to alkyl methyl ethers, produced the ethers in yields as high as 90% Olefins are by-products in these reactions . With ethanol as the solvent, ethyl ethers were formed. Other oxidizing agents (hydrogen peroxide, ozone, /cr/.-butyl hydroperoxide, sodium periodate) did not produce alkyl methyl ethers. 

Oxidation of phenylalkyl phenyl telluriums, in which the phenyltelluro group and the phenyl group are bonded to adjacent carbon atoms, causes a rearrangement the phenyl group takes the place of the phenyltelluro group, and the methoxy group bonds to the carbon atom vacated by the phenyl group .  

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