Cover Picture: Divergent Reactivity of In Situ Generated Metal Azides: Reaction with N, N‐Bis(oxy)enamines as a Case Study (Chem. Eur. J. 19/2017). Issue 19 (16th February 2017)

• Record Type: Journal Article
• Authors: Zhmurov, Petr A.; Khoroshutina, Yulia A.; Novikov, Roman A.; Golovanov, Ivan S.; Sukhorukov, Alexey Yu.; Ioffe, Sema L.
• Is Part Of: Chemistry. Volume 23:Issue 19(2017)
• Page Start: 4464
• Page End: 4464
• Publication Date: 2017-02-16
• Subjects: 1, 2-diamines -- Lewis acids -- metal azides -- nitrogen-oxygen bond -- organic azides; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201700192
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract : In the "chemical billiard" reaction shown on the front cover, a counter ion directs the attack of the azide anion to one or another electrophilic center of the organic substrate. Covalently bonded metal azides transfer N3 − to the β‐carbon atom through a Lewis‐acid‐promoted SN ' process, while ionic azides react through SN 2 attack on the silicon. These two pathways lead to entirely different products. More information can be found in the Full Paper by A. Yu. Sukhorukov et al. onpage 4570 ff.