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Safe radical azidonation using polystyrene supported diazidoiodate(I)

Lavinia Georgeta Marinescu, Christian Marcus Pedersen and Mikael Bols*

*Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 DK-Aarhus, Denmark, Email: bolskemi.ku.dk

L. G. Marinescu, C. M. Pedersen, M. Bols, Tetrahedron, 2005, 61, 123-127.

DOI: 10.1016/j.tet.2004.10.040


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Abstract

Aldehydes are safely and conveniently converted to acyl azides and benzyl ethers to azido ethers by treatment with polymer supported iodine azide in MeCN at 83 °C. The reaction provides an alternative to the use of iodine azide in radical azidonations.

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Radical Azidonation of Aldehydes

L. Marinescu, J. Thinggaard, I. B. Thomsen, M. Bols, J. Org. Chem., 2003, 68, 9453-9455.


Key Words

carbamoyl azides, 1,2-azido ethers, Curtius Rearrangement


ID: J72-Y2005-2770