Regiospecific photochemical transformations of 4, 5-diaryl-Δ4-imidazolin-2-ones: ketal formation and cyclodehydrogenation

Purushothaman, E. ; Rajasekharan Pillai, V. N. (1989) Regiospecific photochemical transformations of 4, 5-diaryl-Δ4-imidazolin-2-ones: ketal formation and cyclodehydrogenation Proceedings of the Indian Academy of Sciences - Chemical Sciences, 101 (5). pp. 391-399. ISSN 0253-4134

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Official URL: http://www.ias.ac.in/j_archive/chemsci/101/vol101c...

Related URL: http://dx.doi.org/10.1007/BF02840673

Abstract

4,5-Diaryl-Δ4-imidazolin-2-ones undergo conversion to 2,2-dialkoxy-4,5-diaryl-Δ4-imidazolines by a characteristic solvent interaction of the carbonyl group on irradiation in alcoholic solvents. The photochemical oxidative cyclization of the stilbene system in these compounds to the corresponding phenanthrene derivatives does not occur under the usual conditions. Acidic conditions hinder the ketal formation of the carbonyl group and favour the oxidative dehydrocyclization reaction to the phenanthrene derivatives. These reactions have been found to be general to the 4,5-diaryl-Δ4-imidazolin-2-ones and plausible mechanistic pathways have been suggested for the two different selective reactions.

Item Type:Article
Source:Copyright of this article belongs to Indian Academy of Sciences.
Keywords:Regiospecific Photochemical Transformations; Photochemical Oxidative Cyclization; Ketal Formation
ID Code:38610
Deposited On:23 May 2011 08:01
Last Modified:17 May 2016 21:24

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