Co-Authors:
Acher, A.J.
Saltzman, S.
Brates, N.
Dunkelblum, E.
Abstract:
The dye-sensitized photolysis of aerated aqueous solutions of terbacil (3-tert-5-chloro-6-methyluracil, I) exposed to solar irradiation was investigated under different reaction conditions. After 2 h of exposure to sunlight, in the presence of methylene blue (3 ppm) or riboflavin (10 ppm), the major photodegradation product in the pH range of 3.0-9.2 was 3-tert-butyl-5-acetyl-5-hydroxyhydantoin (II). In alkaline reaction mixtures (pH 8.0 or 9.2), this product undergoes deacylation, giving 3-tert-5-hydroxyhydantoin (III). In experiments carried out under neutral or acidic conditions (pH 6.8 or 3.0) with riboflavin, two additional products were isolated: a mono-N-dealkylated terbacil dimer (IV) and a nonidentified water-insoluble product (V). The structures of II, III, and IV were determined by using proton and carbon-13 nuclear magnetic resonance, infrared, ultraviolet, and mass spectroscopy. © 1981 American Chemical Society.
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