Abstract
An excess of elemental iodine in N,N-dimethylacetamide enables effective 3/iodanylium-de-hydronation of terminal alkenes with 3-iodopropene derivatives and hydrogen iodide formation within minutes at room temperature. The optimal molar ratio of iodine to substrate was decreased to 1:1 when hydrogen iodide formed was oxidized on a platinum anode. The electrolytic oxidation recovers iodine as a reagent and diminishes the hydrogen iodide inhibitory action to accomplish the monoiodination. The proposed reaction mechanism is based on kinetic measurements and quantum mechanics calculations.
Original language | English (US) |
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Pages (from-to) | 2891-2897 |
Number of pages | 7 |
Journal | Organic and Biomolecular Chemistry |
Volume | 11 |
Issue number | 17 |
DOIs | |
State | Published - May 7 2013 |