University Chemistry ›› 2023, Vol. 38 ›› Issue (5): 211-219.doi: 10.3866/PKU.DXHX202206043

• Chemistry Laboratory • Previous Articles     Next Articles

Visible Light-Induced Metal-Free Catalytic Synthesis of Acetophenone o-Tetrahydrofuran-2-Yl Oxime

Meng Tu1, Xiao-Rui Liu1, Yu-Yun Yin1, Jia-Qi Peng1, Rui-Hua Bai1, Wei Zhang1, Yong-Miao Shen1,2,*()   

  1. 1 Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, China
    2 Key Laboratory of Excited-State Materials of Zhejiang Province, Zhejiang University, Hangzhou 310027, China
  • Received:2022-06-13 Accepted:2022-09-22 Published:2022-10-10
  • Contact: Yong-Miao Shen E-mail:shenym@zstu.edu.cn

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Abstract:

As one of the three basic mechanisms in organic chemistry, the free radical reaction, has been neglected for a long time in experimental teaching, which has led to a disconnection between theory and practice. In this study, o-tetrahydrofuranyl acetophenone oxime ether was synthesized from acetophenone oxime and tetrahydrofuran by a free radical process mediated by carbon tetrachloride under 3 W blue LED light. The products were characterized by NMR, IR and UV spectroscopy. This experiment only requires simple and inexpensive equipment and mild reaction conditions, and has high universality. It teaches the application of bromine radicals in organic synthesis so that students can master their understanding of free radical reactions, and allows them to improve their practical skills by analyzing the molecular structure of the product.

Key words: Acetophenone oxime ether, Free radical reaction, Visible light catalysis, C―O bond formation, Carbon tetrachloride