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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (01): 105-107. 上一篇    下一篇

研究简报

2,5-二甲氧基-4-氯硝基苯与硫化钠的反应

何 庆; 王成云; 姜钦杰; 沈永嘉*   

  1. (华东理工大学精细化工研究所 结构可控先进功能材料及其制备教育部重点实验室 上海 200237)
  • 收稿日期:2008-04-03 修回日期:2008-07-09 发布日期:2009-01-20
  • 通讯作者: 沈永嘉

Reaction of 2,5-Dimethoxy-4-chloronitrobenzene with Sodium Sulfide

He, Qing; Wang, Chengyun; Jiang, Qinjie ; Shen, Yongjia*   

  1. (Laboratory of Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237)
  • Received:2008-04-03 Revised:2008-07-09 Published:2009-01-20
  • Contact: Shen, Yongjia

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2296

被引次数

11

硫化钠和二硫化钠分别在95%乙醇中与2,5-二甲氧基-4-氯硝基苯反应, 原本期望得到2,5-二甲氧基-4-氯苯胺, 然而对产物结构的1H NMR, 13C NMR, MS以及元素分析结果表明, 2,5-二甲氧基-4-氯硝基苯中的硝基没有被硫化钠和二硫化钠还原成氨基, 而是其中的氯原子被硫离子(或二硫离子)取代, 分别生成了4,4’-硫代-2,2’,5,5’-四甲氧基-双硝基苯和4,4’-双硫代-2,2’,5,5’-四甲氧基-双硝基苯. 根据这个实验事实, 讨论了上述亲核取代反应的机理.

关键词: 亲核取代, 2,5-二甲氧基-4-氯硝基苯, 硫化钠, 硝基还原

2,5-Dimethoxy-4-chloronitrobenzene reacted with sodium sulfide or sodium disulfide in 95% ethanol, to expect forming 2,5-dimethoxy-4-chloroaniline. However, the data of 1H NMR, 13C NMR, MS techniques and elemental analyses of the reaction products indicated that no reduction of nitro group in 2,5-dimethoxy-4-chloronitrobenzene happened, instead, a chlorine atom in 2,5-dimethoxy-4-chloronitro- benzene was replaced by sulfur anion or bis-sulfur anion, affording 4,4’-dinitro-2,2’,5,5’-tetramethoxydi- phenyl-sulfur or 4,4’-dinitro-2,2’,5,5’-tetramethoxy-diphenyl-bis-sulfur, respectively. Based on this fact, a mechanism of the nucleophilic substitution reaction is proposed.

Key words: sodium sulfide, reduction for nitro group, nucleophilic substitution, 2,5-dimethoxy-4-chloronitrobenzene