高等学校化学学报

高等学校化学学报 ›› 1995, Vol. 16 ›› Issue (11): 1727.

• 论文 • 上一篇    下一篇

带有致钝取代基的萘衍生物和SO3的反应研究

邹友思, 林静   

  1. 厦门大学化学系, 厦门, 361005
  • 收稿日期:1994-11-14 修回日期:1995-02-09 出版日期:1995-11-24 发布日期:1995-11-24
  • 通讯作者: 邹友思,男,40岁,副教授.
  • 作者简介:邹友思,男,40岁,副教授.
  • 基金资助:

    国家教育委员会留学回国人员科研经费资助

The Reaction of Deactivated Napthalene Derivatives with Sulfur Trioxide

ZOU You-Si, LIN Jing   

  1. Department of Chemistry, Xiamen University, Xianien, 361005
  • Received:1994-11-14 Revised:1995-02-09 Online:1995-11-24 Published:1995-11-24

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摘要： 研究了一系列带有醛基、苯甲酮基、羧基、酯基和硝基等致钝取代基的萘衍生物与SO3的反应。1-萘甲醛的单磺化得到比例为55:9:6:30的5-、6-、7-和8-磺酸取代物。1-苯甲酮萘则以83:11:6的比例得到5-、6-和7-磺酸取代物。1-硝基萘专一地得到5位磺化产物,1-萘甲酸和1-萘甲酸甲酯得到5位和8位取代产物。所有的2位取代萘衍生物均先得到5和8位取代产物,在过量磺化中生成的主产物为5,7-二磺酸取代物,提出了生成SO3络合物及迫位磺化的历程,报道了8-磺酸-1-萘甲酸酐的物理数据。

关键词: 钝化萘衍生物, 三氧化硫, 磺化反应

Abstract: The reaction of sulfur trioxide with deactivated naphthalene derivatives containing an electron withdrawing substituent, viz.-CHO,-COPh,-CO2H, and-CO2Me, indichloromethane as the solvent has been studied by analysis of the resulting mixtures of the sulfo derivatives with 1HNMR,Monosulfonation of 1-formylnaphthalene yields 5-S,6-S,7-Sand 8-S, in a 55: 9:6: 30 ratio, that of 1-benzoylnaphthalene 5-S,6-S and 7-S in a ratio of 83: 11: 6, and 1-nitronaphthalene only 5-S. 1-Naphthoic acid and its methyl ester upon SO3sulfonation and aqueous work-up both yield 5-and 8-sulfonaphthoic acid in a ratio of 65: 35 and 77: 21 respectively. The initially formed peri substituted product is the intramolecular anhydride of 8-sulfo-1-naphthoic acid. All the 2-substituted naphthalenes upon SO3sulfonation yield 5-S and 8-S.

Key words: Deactivated naphthalene derivatives, Sulfo trioxide, Sulfonation

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