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2021 , Vol. 41 >Issue 2: 688 - 694

DOI: https://doi.org/10.6023/cjoc202008018

研究论文

三聚氯氰催化及溶剂效应实现温和高效的酮肟贝克曼重排反应

  • 周婷婷 ,
  • 刘霞 ,
  • 叶子航 ,
  • 周奕鹏 ,
  • 杨雅淇 ,
  • 徐清
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  • 1 温州大学化学与材料工程学院 浙江温州 325035
* Corresponding author. E-mail: qing-xu@wzu.edu.cn

收稿日期: 2020-08-12

  修回日期: 2020-09-18

  网络出版日期: 2020-09-30

基金资助

国家自然科学基金(21672163); 浙江省自然科学基金杰出青年基金(LR14B020002)

收起

Cyanuric Chloride Catalysis and Solvent Effect Leading to a Mild and Efficient Beckmann Rearrangement of Ketoximes

  • Tingting Zhou ,
  • Xia Liu ,
  • Zihang Ye ,
  • Yipeng Zhou ,
  • Yaqi Yang ,
  • Qing Xu
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  • 1 College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035

Received date: 2020-08-12

  Revised date: 2020-09-18

  Online published: 2020-09-30

Supported by

the National Natural Science Foundation of China(21672163); the Natural Science Foundation of Zhejiang Province for Distinguished Young Scholars(LR14B020002)

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摘要

与其他溶剂的效果显著不同, 以六氟异丙醇为溶剂时, 低用量三聚氯氰可在室温下高效催化酮肟的贝克曼重排反应得到相应的酰胺产物. 本方法操作简便, 催化剂用量少, 溶剂可回收再利用, 条件温和, 官能团兼容性好, 适用底物范围广, 产物收率高, 是一种制备酰胺化合物的相对绿色实用的方法.

关键词： 酮肟; 贝克曼重排; 三聚氯氰; 六氟异丙醇; 温和条件; 酰胺

本文引用格式

周婷婷 , 刘霞 , 叶子航 , 周奕鹏 , 杨雅淇 , 徐清 . 三聚氯氰催化及溶剂效应实现温和高效的酮肟贝克曼重排反应[J]. 有机化学, 2021 , 41(2) : 688 -694 . DOI: 10.6023/cjoc202008018

Abstract

By using hexafluoroisopropanol as the solvent, a low loading of cyanuric chloride could effectively catalyze the Beckmann rearrangement of ketoximes to obtain the corresponding amide products under mild conditions, such as room temperature and air atmosphere. The effect of hexafluoroisopropanol was greatly different from that of other solvents. This method has the advantages of simple operation, low catalyst loading, recoverability of solvent, mild conditions, good tolerance of the functional groups, broad substrate scope and high product yields. It is a relatively green and practical method for the preparation of amide compounds.

Key words： ketoxime; Beckmann rearrangement; cyanuric chloride; hexafluoroisopropanol; mild condition; amide

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