高等学校化学学报 ›› 2003, Vol. 24 ›› Issue (12): 2218.

• 研究简报 • 上一篇    下一篇

从苄基型联萘二砜制备dl-二苯并[c,g]菲

安德烈, 谭小华, 彭志鸿, 邵光   

  1. 湖南大学化学化工学院, 长沙 410082
  • 收稿日期:2002-12-25 出版日期:2003-12-24 发布日期:2003-12-24
  • 通讯作者: 安德烈(1957年出生),男,教授,从事有机反应和功能有机化合物研究.E-mail:deliean@sina.com E-mail:deliean@sina.com
  • 基金资助:

    国家自然科学基金(批准号:20272012);教育部博士学科点专项基金(批准号:20020532004)资助

Preparation of dl-Dibenzophenanthrene by Using Benzyl-type Binaphthyl Disulfone

AN De-Lie, TAN Xiao-Hua, PENG Zhi-Hong, SHAO Guang   

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
  • Received:2002-12-25 Online:2003-12-24 Published:2003-12-24

关键词: 联萘二砜, 二苯并[c, g]菲, 反应机理, 分子内亲核取代, 消除反应

Abstract: We reported that a benzyl-type binaphthyl disulfone could be conveniently converted into dibenzophenanthrene. Thus, racemic 1 was treated with lithium diisopropylamide (LDA) afforded dl-dibenzophenanthrene in a moderate yield, together with an unknown benzensulfonyl-substituted derivative 2. The structures were confirmed by MS, 1H, 13CNMR and elemental analysis. The reaction might involve the initiaLIntramolecular nucleophilic substitution to produce an intermediate 3, followed by elimination of benzenesulfinic acid to form dibenzophenanthrene.

Key words: Binaphthyl disulfone, Dibenzophenanthrene, Reaction mechanism, Intramolecular nucleophilic substitution, Elimination=

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