Abstract
Treatment of cinnamyl, 3-methyl-2-butenyl, and 2-cyclohexenyl phenyl tellurides with an oxidizing agent such as H 2O 2, NaIO 4 or t-BuOOH at room temperature under nitrogen affords 1-phenyl-2-propenol, 2-methyl-3-butene-2-ol, and 2-cyclohexenol as a sole or main product respectively in a high yield. The formation of these allylic alcohols can be best explained by assuming a [2,3]-sigmatropic rearrangement of the intermediate allylic telluroxides. These tellurides also react with oxygen, the formation of α.β-unsaturated carbonyl compounds being much increased in this oxidation.
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