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Geminal Diazides Derived from 1,3-Dicarbonyls: A Protocol for Synthesis

Hellmuth Erhardt, Andreas P. Häring, Andreas Kotthaus, Markus Roggel, My Linh Tong, Phillip Biallas, Martin Jübermann, Fabian Mohr and Stefan F. Kirsch*

*Organic Chemistry, Bergische Universität Wuppertal, Gaußstraße 20, 42119 Wuppertal, Germany, Email: sfkirschuni-wuppertal.de

H. Erhardt, A. P. Häring, A. Kotthaus, M. Roggel, M. L. Tong, P. Biallas, M. Jübermann, F. Mohr, S. F. Kirsch, J. Org. Chem., 2015, 80, 12462-12469.

DOI: 10.1021/acs.joc.5b02328 (free Supporting Information)


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Abstract

The reaction of 1,3-dicarbonyl compounds with molecular iodine and sodium azide in aqueous DMSO provides a general access to a broad range of geminal diazides with various structural motifs including sterically demanding substituents and ordinary functional groups. The diazidation of 1,3-dicarbonyls can be selectively achieved even in the presence of other 1,3-dicarbonyls with substituents at 2-position.

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Key Words

1,1-Diazides, α-Azidocarbonyl Compounds, Iodine


ID: J42-Y2015