Direct Conversion of a Benzylic Hydroxy Group into a Selenenyl Group Using the Phenyl Trimethylsilyl Selenide-Aluminum Bromide Combination.

H Abe, A Yamasaki, T Harayama

Index: Abe, Hitoshi; Yamasaki, Akira; Harayama, Takashi Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 8 p. 1311 - 1313

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Citation Number: 8

Abstract

A new reagent system, phenyl trimethylsilyl selenide-aluminum bromide, was developed for the direct conversion of various benzylic hydroxy groups into a selenenyl group. Treatment of cinnamyl alcohol with this reagent system yielded 3, 4-dihydro-4-phenyl-2H-1- benzoselenin via a [3, 3]-sigmatropic rearrangement of the intermediate cinnamyl phenyl selenide.