meso-Reactivity of porphyrins and related compounds. Part 9. Photo-oxygenation of octaethyloxophlorin
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1063-1067
- https://doi.org/10.1039/p19870001063
Abstract
The photo-oxygenation of octaethyloxophlorin has been investigated under basic and under neutral conditions. In both cases unstable intermediate stages are observed spectroscopically. In methanolic sodium methoxide the solution becomes bleached and tetraethyl(methanol)propentdyopent is a significant product. In neutral solutions (e.g. benzene–methanol) the major products are octaethyl-l5,15-dioxo-5,15-dihydroporphyrin (4) and octaethyl-19-formyl-21H,24H-bilin-1,15-dione (7), the formation of octaethyl-21H,24H-bilin-1,19-dione (6) being a minor pathway. A mechanistic rationalisation is proposed.Keywords
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