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Synthesis and photoisomerisation of 2,3,17,18,22-pentamethyl-10,23-dihydro-1,19-[21H,24H]-bilindione, an unsymmetrical bilirubin model compound

✍ Scribed by J. A. de Groot; R. van der Steen; R. Fokkens; J. Lugtenburg

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
476 KB
Volume
101
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

The unsymmetrical bilirubin model compound 2,3,17,18,22‐pentamethyl‐ 10,23‐dihydro‐1,19‐[21H,24H]‐bilindione 1c has been prepared in good yield. Irradiation of 1c leads to a photostationary state which contains three photoproducts in addition to the starting material. The photoproducts have been isolated and fully characterized as the three possible geometric isomers of 1c. Short irradiation of each of the photoisomers shows that a one‐photon one‐double‐bond isomerisation takes place.

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✍ J. A. de Groot; R. van der Steen; J. Lugtenburg 📂 Article 📅 2010 🏛 Elsevier Science 🌐 English ⚖ 443 KB

## Abstract The biliverdinium salt 1 has been prepared in high yield and its behaviour towards nucleophiles studied. The reactions have been found to occur selectively on the central carbon atom 10 and to lead to bilirubin systems. In addition, the photoisomerisation of the bilirubin model compound