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Synthesis 1989; 1989(4): 283-286
DOI: 10.1055/s-1989-27223
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One-Pot Synthesis of Homoallylic Alcohols via a Facile Conversion of Allylic Alcohols into Allylic Iodides

Takaya Kanai* , Shinji Irifune, Yasutaka Ishii, Masaya Ogawa
  • *Department of Applied Chemistry, Faculty of Engineering, Kansai University, Senriyama, Suita, Osaka 564, Japan
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Publication History

Publication Date:
17 September 2002 (online)

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Allylic alcohols were readily converted into allylic iodides by hydrogen iodide generated in situ from chlorotrimethylsilane/sodium iodide and water, or alcohols, under mild conditions. Displacement of allylic alcohols containing a terminal double bond gave allylic iodides accompanied by allylic rearrangement. This procedure has successfully been extended to a one-pot synthesis of homoallylic alcohols by carrying out successive Barbier type reactions.

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