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]
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