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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
Iodine(III)-Mediated Diazidation and Azido-oxyamination of Enamides
Sophie Nocquet-Thibault1, Anita Rayar1, Pascal Retailleau1
1Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, LabEx LERMIT, Avenue de la Terrasse, 91198 Gif-sur-Yvette (France), Fax: (+33) 1-6907-7247.
Abstract:
In this study we demonstrate that the combination of bis(tert-butylcarbonyloxy)iodobenzene and lithium azide in acetonitrile allows the diazidation of various enamide substrates. The azido-oxyamination of the same substrates can be carried out in the presence of 2,2,6,6-tetramethylpiperidine N-oxide (TEMPO). Control experiments strongly suggest that this latter process occurs through a shift in nature of the in situ generated electrophilic species from a radical to a cation. Finally, the versatility of the novel compounds synthesized was also assessed by running various selective reactions on them.
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