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Synthesis and interaction with human serum albumin of the first 3,18-disubstituted derivative of bilirubin

Painter, Leoni; Harding, Margaret; Beeby, Philip J


Addition of excess (>500 equiv.) of p-fluorothiophenol to bilirubin in the presence of toluene-p-sulfonic acid catalyst afforded 3,18-didevinyl-3,18-bis[2-(p-fluorothiophenyl)ethyl] billrubin 2 from anti-Markovnikov addition to both the exo and endo vinyl groups of bilirubin. Toluene-p-sulfonic acid is not essential as p-fluorothiophenol acts as the acid and nucleophile in the reaction. In contrast, In the presence of toluene-p-sulfonic acid, regioselective Markovnlkov addition of thloacetic...[Show more]

CollectionsANU Research Publications
Date published: 1998
Type: Journal article
Source: Journal of the Chemical Society, Perkin Transactions 1


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