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