Selective Bromination of Polyenes with TBCO (2, 4, 4, 6-tetrabromocyclohexadienone)

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  • KATO Tadahiro
    Department of Chemistry, Faculty of Science, Tohoku University
  • ICHINOSE Isao
    Department of Chemistry, Faculty of Science, Tohoku University
  • HOSOGAI Takeo
    Department of Chemistry, Faculty of Science, Tohoku University

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  • 新しい試薬　　ＴＢＣＯ（２，４，４，６‐ｔｅｔｒａｂｒｏｍｏｃｙｃｌｏｈｅｘａｄｉｅｎｏｎｅ）によるポリエンの選択的臭素化反応
  • TBCO 2 4 4 6 tetrabromocyclohexadienone

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Description

In connection with a program directed toward the biogenetic type synthesis of bromine containing terpenoids, we have searched a new reagent system and found that 2, 4, 4, 6-tetrabromocyclohexadienone (TBCO) is effective for bromination of polyenes. Reaction fashion of TBCO can be divided into four types. 1. Dibromination, , 2. Brominative cyclization, 3. Bromo etherification of polyene alcohol and ketone, and 4. Bromohydrin formation in the presence of ROH. Details are described.

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