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Issue 17, 2013
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Electrophilic monoiodination of terminal alkenes

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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.

Graphical abstract: Electrophilic monoiodination of terminal alkenes

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Article information


Submitted
03 Dec 2012
Accepted
20 Feb 2013
First published
21 Feb 2013

Org. Biomol. Chem., 2013,11, 2891-2897
Article type
Paper

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

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