A Convenient Method for the Iodination of Alcohols with Triphenylphosphine-Carbon Tetrachloride and Sodium Iodide

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  • MIYANO Sotaro
    Department of Applied Chemistry, Faculty of Engineering, Tohoku University;
  • USHIYAMA Hidehiko
    Department of Applied Chemistry, Faculty of Engineering, Tohoku University;
  • HASHIMOTO Harukichi
    Department of Applied Chemistry, Faculty of Engineering, Tohoku University;

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Other Title
  • トリフェニルホスフィンー四塩化炭素一ヨウ化ナトリウムによるアルコールのヨウ素化反応
  • トリフェニルホスフィン‐四塩化炭素‐よう化ナトリウムによるアルコールのよう素化反応

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Description

The combination of triPhenylphosphine and carbon tetrachloride has been utilized widely for the chlorination of alcohol under mild conditions. The presence of sodium iodide in this reaction system provides a convenient route for the synthesis of primary and secondary alkyl iodides (Table 1). Primary alcohols reacted smoothly within 1.5 hr at ambient temperature to afford the corresponding iodides in excellent yields. Iodination of secondary alcohols required somewhat higher temperature and longer reaction time, but no significant amount of rearranged or chlorinated products was formed (less than 3%).

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1977 (1), 138-140, 1977-01-10

    The Chemical Society of Japan

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