Photoinduced debenzylation of 2, 5-bis(dibenzylamino)-3, 6-dichloro-p-benzoquinone. (September 2017)

• Record Type: Journal Article
• Authors: Shin, In-Sub; Shimada, Yuta; Ishihara, Shinji; Horiguchi-Babamoto, Emi; Matsumoto, Shinya
• Is Part Of: Dyes and pigments. Volume 144(2017)
• Page Start: 110
• Page End: 118
• Publication Date: 2017-09
• Subjects: Aminobenzoquinone -- Photoreaction -- Benzyl group -- Photoelimination -- Sunlight -- Radical reaction; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2017.05.028
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: 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. Graphical abstract: Highlights: 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.