Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 30, Pages 7913-7917Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201402433
Keywords
azides; energy-rich compounds; hypervalent iodine compounds; nitrogen; oxidation
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Funding
- DFG [KI 1289/2-2]
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Three simple methods for the synthesis of geminal triazides are described: Starting from 1) 3-oxocarboxylic acids, 2) iodomethyl ketones, or 3) terminal olefins, a range of triazidomethyl ketones can be constructed under mild oxidative reaction conditions by the use of IBX-SO3K, a sulfonylated derivative of 2-iodoxybenzoic acid (IBX), and NaN3 as an azide source. This is the first report of representatives of this novel class of triazide compounds: Despite their high nitrogen content, the geminal triazides are easy to handle, even when preparative-scale syntheses are performed. (Caution: These procedures still require protective measures!) The triazides are now broadly available for further studies regarding their properties and reactivity. Furthermore, we show how the method can be used to provide alpha-azidoesters, which are potential building blocks for amino acids.
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