103999-80-0Relevant articles and documents
An efficient and improved procedure for preparation of triflyl azide and application in catalytic diazotransfer reaction
Yan, Ri-Bai,Yang, Fan,Wu, Yanfen,Zhang, Li-He,Ye, Xin-Shan
, p. 8993 - 8995 (2005)
An efficient and improved procedure for preparation of triflyl azide and application in catalytic diazotransfer reaction are described. The amount of highly toxic reagents NaN3 and Tf2O, is significantly reduced comparing with the pr
The synthesis of α-azidoesters and geminal triazides
Klahn, Philipp,Erhardt, Hellmuth,Kotthaus, Andreas,Kirsch, Stefan F.
supporting information, p. 7913 - 7917 (2014/08/05)
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 α-azidoesters, which are potential building blocks for amino acids. Either/or: Geminal triazides are rapidly constructed with broad scope by the use of oxocarboxylic acids, iodomethyl ketones, or terminal olefins as starting substrates in oxidative azidations with a mild derivative of 2-iodoxybenzoic acid and sodium azide. Along with this little-studied class of organic azides, α-azidoesters were also synthesized.
New one-carbon degradative transformation of β-alkyl-β-azido alcohols
Fan, Qiu-Hua,Ni, Nan-Ting,Li, Qin,Zhang, Li-He,Ye, Xin-Shan
, p. 1007 - 1009 (2007/10/03)
A new transformation of 2-azido-1-hydroxy-containing compounds to nitriles with one carbon less than the starting materials by oxidation was reported. The reaction can be performed under mild conditions.