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Synlett 1995; 1995(10): 1081-1082
DOI: 10.1055/s-1995-5173
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Direct Azidation of Adamantane and Norbornane by Stable Azidoiodinanes

Alexei P. Krasutsky, Chris J. Kuehl, Viktor V. Zhdankin*
  • *Chemistry Department, University of Minnesota-Duluth, Duluth, Minnesota 55812, USA
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Publication Date:
31 December 2000 (online)

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Stable azidoiodinanes 1 and 2 react with norbornane, adamantane and 1,3-dimethyladamantane upon heating in the presence of catalytic amounts benzoyl peroxide with the formation of the respective azides 6-8 in moderate yields. In these reactions, reagent 2 can be generated in situ from 2-iodosobenzoic acid and azidotrimethylsilane, and used without isolation.

azidoiodinane - iodine - azides - 1-azidoadamantane - 2-azidonorbornane