Chinese Journal of Applied Chemistry
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JIN Zhenkang,LIU Hewen()
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Abstract:
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.
Key words: cyclophane, cyclophanealdehyde, ultraviolet irradiation
JIN Zhenkang, LIU Hewen. Synthesis of Cyclophanealdehyde by Ultraviolet Irradiation[J]. Chinese Journal of Applied Chemistry.
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http://yyhx.ciac.jl.cn/EN/Y2019/V36/I12/0