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- Title
Photolyse des 3-Phenyl-2, 1-benzisoxazols und einiger seiner Derivate in Salzsäure bzw. Schwefelsäure.
- Authors
Giovannini, Edgardo; De Sousa, Bernardo F. S. E.
- Abstract
Photolysis of 3-phenyl-2,1-benzisoxazole and some derivates in hydrochloric and sulfuric acid The photolysis of 3-phenylanthranils (3-phenyl-2, 1-benzisoxazoles) in conc. hydrochloric or sulfuric acid leads to the formation of 5-substituted 2-amino-benzophenones wherein the 5-substituent is the anion of the acid employed. 5-Halo-substituted 3-phenylanthranils, however, show a differing reaction pattern in the two acids. Whereas 2-amino-3, 5-dihalo-benzophenones are obtained when photolysis is effected in conc. hydrochloric acid, irradiation in sulfuric acid causes the hydroxy group to substitute the halogen which migrates to the 4-position of the 2, 1-benzisoxazole to yield 2-amino-5-hydroxy-6-halo-benzophenones. A similar behaviour in sulfuric acid is also observed with 5, 7-dichloro-3-phenylanthranil. When the 5-position of the anthranil is blocked by a phenyl group, irradiation in conc. hydrochloric acid leads to entry of the halogen mainly in this 5-phenyl substituent, as can be expected from mesomeric structures. The reaction mechanisms for the photolytic behaviour of 3-phenylanthranils in both conc. hydrochloric and sulfuric acid is discussed.
- Publication
Helvetica Chimica Acta, 1979, Vol 62, Issue 1, p185
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19790620127