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Synthesis 1988; 1988(3): 175-178
DOI: 10.1055/s-1988-27505
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Ring Opening of Tetrahydrofurans with Phenyl Trimethylsilyl Selenide Catalyzed by Moist Zinc Iodide

Noritaka Miyoshi* , Yoshio Hatayama, Ilhyong Ryu, Nobuaki Kambe, Toshiaki Murai, Shinji Murai, Noboru Sonoda
  • *Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565, Japan
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Publication Date:
20 August 2002 (online)

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Phenyl trimethylsilyl selenide (1) reacted with tetrahydrofurans 2 in dichloromethane in the presence of a catalytic amount of zinc iodide to give ring opened silyl ethers of δ-phenylseleno alcohols 3 in good yields. It was found that well-dried zinc iodide catalyzed the reaction less effectively than moisturized zinc iodide, prepared by treatment of the reagent with water-saturated hexane.