Photoinduced debenzylation of 2,5-bis(dibenzylamino)-3,6-dichloro-p-benzoquinone

•The photoreaction of 2,5-bis(dibenzylamino)-3,6-dichloro-p-benzoquinone was investigated.•Two new reaction products were separated and characterized.•One of the new products was converted into the two reported debenzylated analogues.•The photoreaction was found to occur under sunlight irradiation.•A possible mechanism of this photoreaction was demonstrated.

In this detailed study of the photoreaction of 2,5-bis(dibenzylamino)-3,6-dichloro-p-benzoquinone, two new products were separated along with the previously reported debenzylated analogues, and their molecular structure was determined. One compound was identified as 2-(benzylamino)-3,6-dichloro-5-(dibenzylamino)-p-benzoquinone, which was found to undergo further debenzylation to form the two known debenzylated analogues. The other compound was identified as the hydroquinone form of the starting material. This photoreaction was examined in detail using various analytical techniques under different experimental conditions, and a plausible reaction pathway was proposed on the basis of the experimental results. In addition, the reaction was found to occur also under sunlight irradiation.

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