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The international journal for inorganic, organometallic and bioinorganic chemistry
Paper
Article citation: Jiadi Zhang, Dalton Trans., 2010, DOI: 10.1039/b912219b
Reactivity and kinetic–mechanistic studies of regioselective reactions of rhodium porphyrins with unactivated olefins in water that form
-hydroxyalkyl complexes and conversion to ketones and epoxidesJiadi Zhang, Bradford B. Wayland, Lin Yun, Shan Li and Xuefeng Fu
This article reports on the selective oxidation of unactivated alkenes to ketones and epoxides through the intermediacy of
-hydroxyalkyl rhodium porphyrin complexes which are formed by reactions of terminal alkenes with tetra(p-sulfonatophenyl)porphyrin rhodium(III) complex. The -hydroxyalkyl rhodium porphyrin complexes in water undergo -C–H elimination to produce ketones in aqueous pH 9.0 solutions and O–H deprotonation in KOH/DMSO solutions resulting in the rapid and quantitative intramolecular nucleophilic displacement to form 1,2-epoxyalkanes.
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