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) |
|---|---|
| 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 |