ALLYLIC ALCOHOLS FORMATION BY OXIDATION OF ALLYLIC PHENYL TELLURIDES. A POSSIBLE SIGMATROPIC REARRANGEMENT OF ALLYLIC TELLUROXIDES

Article abstract of DOI:10.1016/S0040-4039(00)61965-2

Treatment of cinnamyl, 3-methyl-2-butenyl, and 2-cyclohexenyl phenyl tellurides with an oxidizing agent such as H2O2, NaIO4, 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.