高等学校化学学报

高等学校化学学报 ›› 1994, Vol. 15 ›› Issue (2): 216.

• 论文 • 上一篇    下一篇

一种新型的芳基重排反应(Ⅱ)──苯并环己酮中β-芳基的重排

李良助, 赵秀敏, 赵亚军, 袁晋芳   

  1. 北京大学化学系, 北京, 100871
  • 收稿日期:1993-03-08 修回日期:1993-08-10 出版日期:1994-02-24 发布日期:1994-02-24
  • 通讯作者: 赵亚军
  • 作者简介:李良助,男,58岁,副教授.
  • 基金资助:

    国家自然科学基金

A Novel Aryl Rearrangement Reaction(Ⅱ) ──β-Aryl Rearrangement in the Tetral-1-ones

LI Liang-Zhu, ZHAO Xiu-Min, ZHAO Ya-Jun, YAUN Jin-Fang   

  1. Department of Chemistry, Peking University, Beijing, 100871
  • Received:1993-03-08 Revised:1993-08-10 Online:1994-02-24 Published:1994-02-24

PDF (PC)

摘要： 报道了3-芳基四氢合萘-1-酮的烯醇硅醚在氧化碘苯-三氟化硼的协同作用下3-位芳基迁移到2-位,生成2-芳基-3-氟四氢合萘-1-酮的反应。当芳基是Ph-p-Cl-Ph、p-Me-Ph和p-MeO-Ph时,收率分别为80%、61%、10%和5%,并讨论了这一反应的机理。

关键词: 四氢合萘酮, 烯醇硅醚, 芳基重排, 氧化碘苯-三氟化硼

Abstract: The aryl group of 3-aryltetral-1-ones was shifted to position-2 yielding 2-aryl-3-fluorotetral-1-ones when the enol silyl ethers derived from the 3-aryltetral-1-ones were treated with iodosobenzene- borontrifluoride complex(PhIO·BF3).As the aryl was Ph-,p-Cl-Ph-, p-Me-Ph-, and p-MeO-Ph-, the yields of the products was 80%, 61%, 10% and 5% respectively.The rearrangement mechanism was suggested to be a successive process.the end silyl ether 2 reacts with PhIO·BF3 to form an intermediate 6.3-Aryl group has a backside migration to C-2which is deficient in electron as iodine atom departs from it, and the fluorine atom attakcts C-3while the heterolysis of fluorine-boron bond is completed.

Key words: Tetral-1-one, Enol silyl ether, Aryl rearrangement, Iodosobenzene-borontrifluoride

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