Citation: Fan Xin, Yi Rong, Wang Fang, Zhang Xu, Xu Qing, Yu Lei. Copper-Catalyzed Selectivity-Switchable Dehydration/Beckmann Rearrangement Reactions of Aldoxime[J]. Chinese Journal of Organic Chemistry, ;2018, 38(10): 2736-2740. doi: 10.6023/cjoc201805044 shu

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

Corresponding author: Zhang Xu, zhangxu@yzu.edu.cn Yu Lei, yulei@yzu.edu.cn
Received Date: 22 May 2018
Revised Date: 11 June 2018
Available Online: 15 October 2018
Fund Project: the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) and the Natural Science Foundation of Guangling College ZKZD17005the National Natural Science Foundation of China 21202141Project 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)

Figures(2)

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.
- aldoxime,
- dehydration,
- Beckmann rearrangement,
- nitrile,
- amide
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