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Regiospecific Azidoiodination of Alkenes with Sodium Periodate, Potassium Iodide, and Sodium Azide: A High-Yield Synthesis of β-Iodoazides

Pandurang V. Chouthaiwale, Pratibha U. Karabal, Gurunath Suryavanshi, Arumugam Sudalai*

*Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune 411 008, India, Email:

P. V. Chouthaiwale, P. U. Karabal, G. Suryavanshi, A. Sudalai, Synthesis, 2010, 3879-3882.

DOI: 10.1055/s-0030-1258250

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The combination of sodium periodate, potassium iodide, and sodium azide is an efficient, simple, and inexpensive reagent system for azidoiodination of alkenes. The regiospecific 1,2-azidoiodination proceeds in an anti-Markovnikov fashion to produce β-iodoazides in excellent yields.

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Key Words

azides, iodides, alkenes, azidoiodination, β-iodoazides, regio­specific, sodium periodate

ID: J66-Y2010-3290