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One-Pot Synthesis of Homoallylic Alcohols via a Facile Conversion of Allylic Alcohols into Allylic Iodides

T Kanai, Shinji Irifune, Yasutaka Ishii, Masaya Ogawa

Abstract

All articles of this category 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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Key concepts: Allylic rearrangement, Chemistry, Hydrogen iodide, Sodium iodide, Iodide, Organic chemistry, Iodine, Double bond