Tetrahedron Letters p. 921 - 924 (1985)
Update date:2022-08-03
Topics:
Uemura, Sakae
Fukuzawa, Shin-ichi
Ohe, Kouichi
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.
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(2020)
