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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