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Photochemical isomerization of 2-(N-phenylamino)-2-phenyl-1,3-indandione

P. Hrnčiar, A. Gáplovský, E. Jankulicová, and J. Donovalová

Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, CS-84215 Bratislava

 

Abstract: Photochemical isomerization of 2-(N-phenylamino)-2-phenyl-l,3-indandione was studied at two different wavelengths λxc > 360 nm and λхс = 254 nm. In both cases the same products 3-[(N-phenylamino)phenylmethylene]phthalide, N-phenylphthalimide, N-phenylbenzamide, and 1,4-dioxo-2,3-diphenyl-l,2,3,4-tetrahydroisoquinoline were formed, however in a different percentage proportion in each case. After light has been absorbed,  α-cleavage takes place, followed by formation of the above com­ pounds. The emission spectra of the starting compound recorded in metha­nol and in hexane revealed minimal dependence of fluorescence maximum on solvent polarity.

Full paper in Portable Document Format: 421a53.pdf

 

Chemical Papers 42 (1) 53–58 (1988)

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