Copper-Catalyzed Selectivity-Switchable Dehydration/Beckmann Rearrangement Reactions of Aldoxime

doi:10.6023/cjoc201805044

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (10): 2736-2740.DOI: 10.6023/cjoc201805044 Previous Articles Next Articles

Notes

铜催化醛肟脱水/贝克曼重排选择性可切换反应

范昕^a,b, 易容^a,b, 王芳^c, 张旭^a,b, 徐清^a,b, 俞磊^a,b

a 扬州大学广陵学院扬州 225000;
b 扬州大学化学化工学院扬州 225002;
c 扬州工业职业技术学院扬州 225127

收稿日期:2018-05-22 修回日期:2018-06-11 发布日期:2018-06-15
通讯作者: 张旭,E-mail:zhangxu@yzu.edu.cn;俞磊,E-mail:yulei@yzu.edu.cn E-mail:zhangxu@yzu.edu.cn;yulei@yzu.edu.cn
基金资助:
国家自然科学基金（No.21202141）、江苏省高校优势学科项目及广陵学院自然科学基金（No.ZKZD17005）资助项目.

Copper-Catalyzed Selectivity-Switchable Dehydration/Beckmann Rearrangement Reactions of Aldoxime

Fan Xin^a,b, Yi Rong^a,b, Wang Fang^c, Zhang Xu^a,b, Xu Qing^a,b, Yu Lei^a,b

a Guangling College, Yangzhou University, Yangzhou 225000;
b School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002;
c Yangzhou Polytechnology Institute, Yangzhou 225127

Received:2018-05-22 Revised:2018-06-11 Published:2018-06-15
Contact: 10.6023/cjoc201805044 E-mail:zhangxu@yzu.edu.cn;yulei@yzu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21202141), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) and the Natural Science Foundation of Guangling College (No. ZKZD17005).

1. Copper-Catalyzed Selectivity-Switchable Dehydration/Beckmann Rearrangement Reactions of Aldoxime.PDF(298KB)

Abstract

It was found that, copper as a cheap metal, could well catalyze the dehydration reaction of aldoximes to organonitriles in nitrile solvent by using MnO₂ as the co-catalyst and PPh₃ as the ligand. In contrast, instead of organonitriles, the Cu-catalyzed reactions of the aldoximes in water led to amides, which were the products of the Beckmann rearrangements. These interesting selectivity-switchable reactions afford easy accesses to the related useful organic compounds and may be of both academic and practical values.

Key words: aldoxime, dehydration, Beckmann rearrangement, nitrile, amide

Cite this article

Fan Xin, Yi Rong, Wang Fang, Zhang Xu, Xu Qing, Yu Lei. Copper-Catalyzed Selectivity-Switchable Dehydration/Beckmann Rearrangement Reactions of Aldoxime[J]. Chin. J. Org. Chem., 2018, 38(10): 2736-2740.

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铜催化醛肟脱水/贝克曼重排选择性可切换反应

Copper-Catalyzed Selectivity-Switchable Dehydration/Beckmann Rearrangement Reactions of Aldoxime

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