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Synthesis 2010(22): 3879-3882  
DOI: 10.1055/s-0030-1258250
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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
Fax: +91(20)25902676; e-Mail: a.sudalai@ncl.res.in;
Further Information

Publication History

Received 19 July 2010
Publication Date:
14 September 2010 (online)

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Abstract

The combination of sodium periodate, potassium iodide, and sodium azide has been found to be 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.

Key words

azides - alkenes - azidoiodination - β-iodoazides - regio­specific

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