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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Badger G M, Drewer R J and Lewis G E 1966Aust. J. Chem. 19 643
Becker H D 1970J. Org. Chem. 35 2099
Copper J L and Wasserman H H 1969Chem. Commun. 200
Grimshaw J and Mannus D 1977J. Chem. Soc. Perkin I 1096
Maliory F B, Gordan J T and Wood C S 1963J. Am. Chem. Soc. 85 828
Padwa A and Hartman R 1966J. Am. Chem. Soc. 88 3759
Pillai V N R and Purushothaman E 1978Curr. Sci. 47 627
Pillai V N R and Ravindran M 1977Indian J. Chem. B15 1043
Rees C W and Sale A A 1973J. Chem. Soc. Perkin I 6 545
Steffen G and Schenck G O 1967Chem. Ber. 100 3961
Winans C F and Adkins H 1933J. Am. Chem. Soc. 55 4167
Wood C S and Mallory F B 1964J. Org. Chem. 29 3373
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Purushothaman, E., Pillai, V.N.R. Regiospecific photochemical transformations of 4, 5-diaryl-Δ4imidazolin-2-ones: ketai formation and cyclodehydrogenation. Proc. Indian Acad. Sci. (Chem. Sci.) 101, 391–399 (1989). https://doi.org/10.1007/BF02840673
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02840673