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有机化学
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有机化学 ›› 1998, Vol. 18 ›› Issue (5): 465-468. 上一篇    下一篇

研究论文

荧光素和苯磺酰氯间反应机理研究

欧阳直熏;陈德华;袁希召   

  1. 香港中文大学化学系;武汉大学分析测试中心.武汉(430072)
  • 发布日期:1998-10-25

Study on the reaction mechanism between fluorescein and phenylsulfonic acid chloride

Ou Yangzhixun;Chen Dehua;Yuan Xizhao   

  1. Wuhan Univ., Center of Anal Measur.Wuhan(430072)
  • Published:1998-10-25

被引次数

19

在N,N-二甲基甲酰胺存在下,荧光素和苯磺酰氯间的反应经历串联两步:首先荧光素被苯磺酰氯酯化,然后生成的氯离子亲核进攻芳碳,取代苯磺酰氧基,后者是良好的离去基团。反应的结果是氯取了荧光素的酚羟基,反应机理由本工作找到的关键中间体证实。

关键词: 苯磺酸P, 酰氯P, 荧光素, 质谱法, 二甲基甲酰胺, 中间体, 反应机理

In the presence of N, N-dimethylformamide, the reaction between fluorescein and phenylsulfonyl chloride proceeds with two consecutive steps: first, fluorescein is esterified with phenylsulfonyl chloride, and chloride ion formed nucleophilically attacks aryl carbon and then substitutes for phenylsulfonyloxy, which is a good leaving group. Whole effect of the reaction is that the substitution of chlorine for phenolic hydroxy on fluorescein. The reaction mechanism is certificated by the key intermediate found in the work.

Key words: BENZENESULFONIC ACID P, MASS SPECTROGRAPHY, INTERMEDIATE, DIMETHYLFORMAMIDE, ACYL CHLORIDES P, LUCIFERIN, REACTION MECHANISM

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