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Paper | Regular issue | Vol 87, No. 6, 2013, pp.1289-1299
Published online, 2nd May, 2013
DOI: 10.3987/COM-13-12721
Thermal and Photochemical Rearrangements of 3-Arylamino-2-phenyl-1H-inden-1-ones to N-Arylphthalimides

Masayuki Kawai, Eriko Sakanoshita, Motoko Akita, and Keiji Kobayashi*

*Department of Chemistry, Faculty of Science, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan

Abstract

Upon heating to above their melting temperatures, 3-arylamino-2-phenyl-1H-inden-1-ones and 2,2’-diphenyl-3,3’-bis(arylimino)- [2,2’-bi-1H-indene]-1,1’-dione undergo a skeletal rearrangement to afford N-arylphthalimides along with benzoic acid in the presence of atmospheric oxygen. The photoreaction of these compounds in acetonitrile also results in the formation of these products. The mechanism of these reactions, including the formation of a peroxyl radical followed by its conversion to a nitrogen-centered radical, is proposed.