Tetrahedron letters

Allylic alcohols formation by oxidation of allylic phenyl tellurides. A possible [2, 3] sigmatropic rearrangement of allylic telluroxides

S Uemura, S Fukuzawa, K Ohe

Index: Uemura, Sakae; Fukuzawa, Shin-ichi; Ohe, Kouichi Tetrahedron Letters, 1985 , vol. 26, # 7 p. 921 - 924

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Citation Number: 20

Abstract

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