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Citation: JIN Zhenkang, LIU Hewen. Synthesis of Cyclophanealdehyde by Ultraviolet Irradiation[J]. Chinese Journal of Applied Chemistry, ;2019, 36(12): 1371-1375. doi: 10.11944/j.issn.1000-0518.2019.12.190147 shu

Synthesis of Cyclophanealdehyde by Ultraviolet Irradiation

JIN Zhenkang ,
LIU Hewen ^,

School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, China

Corresponding author: LIU Hewen, lhewen@ustc.edu.cn
Received Date: 20 May 2019
Revised Date: 26 July 2019
Accepted Date: 9 October 2019

Fund Project: Supported by the National Natural Science Foundation of China(No.51673181)the National Natural Science Foundation of China 51673181

Figures(7)

In this paper, the chloroform solution of[2.2]paracyclophane is irradiated under 254 nm ultraviolet light to yield two main products, i.e. 4-formyl[2.2]paracyclophane and 4, 4'-(ethane-1, 2-diyl)dibenzaldehyde. The structures of the products are characterized by nuclear magnetic resonance spectroscopy (NMR), gas chromatography-mass spectrometer (GC-MS). The reaction conditions are explored. The coexistence of chloroform and water is important to form the aldehyde products and a possible reaction mechanism that the CHCl₂· radical is added to the benzene ring and further forms an aldehyde group by Reimer-Tiemann reaction is proposed.
- cyclophane,
- cyclophanealdehyde,
- ultraviolet irradiation
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