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

Abstract

In this detailed study of the photoreaction of 2,5-bis(dibenzylamino)-3,6dichloro-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 2 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.

Two polymorphs of 2,5-dichloro-3,6-bis(dibenzylamino)-p-hydroquinone with flexible dibenzylamino groups

“…Compound (1) ( Fig. 1) was synthesized following the procedure reported by Shin et al (2017), and its chemical structure was confirmed by conventional analytical techniques. The crystallization of (1) was carried out by the liquidliquid diffusion method in a thin glass tube, using a combi-nation of chloroform (good solvent) and methanol/ethanol (poor solvent).…”

“…However, we could also prepare significant amounts of (1b) by crystallization of the quinone form of (1), which was also carried out by liquid-liquid diffusion, using a combination of chloroform and n-hexane as the good and poor solvents, respectively. The quinone form of (1) was transformed into the hydroquinone form by ambient light during crystallization (Shin et al, 2017). Thus, in contrast to the direct crystallization of (1), a considerable quantity of (1b) was obtained by this method.…”

Photocatalytic Strategy to Realize N-Debenzylation via Aerobic Oxidation Catalyzed by 4CzIPN

“…On the way to sustainable development, photocatalytic oxidation with molecular oxygen offers a promising strategy for green synthesis with reduced pollutants and energy consumption. − The benzyl group has been widely utilized as a protecting group for wide applications in the multistep synthesis of drugs, , dyes, , fine chemicals, and energetic materials, − resulting in widespread attention to debenzylation.…”