Tetrahedron p. 1893 - 1908 (1983)
Update date:2022-07-30
Topics:
Landen, G. L.
Park, Y. -T.
Lightner, D. A.
4-Ethyl-3-methyl-5-(4-ethyl-3,5-dimethylpyrrolyl-2-methylidene)-3-pyrrolin-2-one (1), 3,4-diethyl-5-(4-ethyl-3,5-dimethylpyrrolyl-2-methylidene)-3-pyrrolin-2-one (2) and xanthobilirubinic acid (XBR) undergo self-sensitized photo-oxygenation, as does bilirubin.The reaction products of 1 consist of methylethylmaleimide, kryptopyrrole aldehyde and its photo-oxygenation product and oxygenated dipyrroles.The same products are formed from 2, except xeronimide is found instead of methylethylmaleimide.Kinetic studies indicate that singlet oxygen is not necessarily involved in the photo-oxygenation reactions.Geometric photoisomerization (Z<*>E) of 1 and 2, and XBR proceeds at an even faster rate than photosensitized oxygenation.
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