title: The synthesis of α-azidoesters and geminal triazides.
abstract: 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-SO3 K, 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 α-azidoesters, which are potential building blocks for amino acids.
authors.affiliation: Organic Chemistry, Bergische Universität Wuppertal, Gaussstrasse 20, 42119 Wuppertal (Germany).
authors.forename: Philipp
authors.initials: P
authors.lastname: Klahn
authors.forename: Hellmuth
authors.initials: H
authors.lastname: Erhardt
authors.forename: Andreas
authors.initials: A
authors.lastname: Kotthaus
authors.forename: Stefan F
authors.initials: SF
authors.lastname: Kirsch
mesh_terms: D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D001386:Azides; D004952:Esters; D009584:Nitrogen
keywords: azides; energy-rich compounds; hypervalent iodine compounds; nitrogen; oxidation