Jump to main content
Jump to site search

Issue 17, 2013
Previous Article Next Article

Electrophilic monoiodination of terminal alkenes

Author affiliations


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.

Graphical abstract: Electrophilic monoiodination of terminal alkenes

Back to tab navigation

Supplementary files

Publication details

The article was received on 03 Dec 2012, accepted on 20 Feb 2013 and first published on 21 Feb 2013

Article type: Paper
DOI: 10.1039/C3OB27348B
Citation: Org. Biomol. Chem., 2013,11, 2891-2897
  •   Request permissions

    Electrophilic monoiodination of terminal alkenes

    S. V. Yemets, T. E. Shubina and P. A. Krasutsky, Org. Biomol. Chem., 2013, 11, 2891
    DOI: 10.1039/C3OB27348B

Search articles by author