物理化学学报 >> 1990, Vol. 6 >> Issue (06): 699-705.doi: 10.3866/PKU.WHXB19900612

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3-巯基香豆素和二苯胺的α-氨甲基化反应(Mannich反应)的动力学研究

何大淹; 邢其毅; 金声; 吕木坚   

  1. 北京大学化学系
  • 收稿日期:1989-04-02 修回日期:1990-05-24 发布日期:1990-12-15
  • 通讯作者: 邢其毅

KINETIC STUDY OF THE MANNICH REACTION OF 3-THIOLCOUMARIN WITH DIPHENYLAMINE

He Da-Yan; Xing Qi-Yi; Jin Sheng; Lu Mu-Jian   

  1. Department of Chemistry; Peking University
  • Received:1989-04-02 Revised:1990-05-24 Published:1990-12-15
  • Contact: Xing Qi-Yi

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摘要： 通过实验及动力学研究, 证明-3巯基香豆素(6)和二苯胺发生α-氨甲基化反应时, 是(6)首先和甲醛反应, 生成S-半缩醛——3-羟甲硫基香豆素(7), 然后再与二苯胺反应形成3-二苯胺甲硫基香豆素(8), 3-羟甲硫基香豆素与二苯胺在冰醋酸的催化作用下进行反应时, 随着酸浓度的改变, 反应机理发生了改变, 本文对这一反应机理进行了讨论和解释。

Abstract: A kinetic study of the Mannich reaction of 3-thiolcoumarin with diphenylamine was studied. It was found that the mechanism of this reaction is different from the classical mechanism of Mannich reaction. 3-Thiolcoumarin first condenses with form-aldehyde to produce 3-hydroxy-methylthiocoumarin which then reacts with diphenyl-amine with the formation of the a-aminomethylated thioether. The reaction appears to be third order at low concentrations (below 0.2 mol·L~(-1)) and first order at higher concentrations (above 0.35 mol·L~(-1)) of the acetic acid used in the acid catalysis.