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The Synthesis of α‐Azidoesters and Geminal Triazides
Author(s) -
Klahn Philipp,
Erhardt Hellmuth,
Kotthaus Andreas,
Kirsch Stefan F.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201402433
Subject(s) - geminal , reactivity (psychology) , azide , chemistry , combinatorial chemistry , organic chemistry , derivative (finance) , nitrogen , medicine , alternative medicine , pathology , financial economics , economics
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‐SO 3 K, a sulfonylated derivative of 2‐iodoxybenzoic acid (IBX), and NaN 3 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.