D. J. Anderson, C. Muchmore
Jul 1, 1995
Citations
1
Influential Citations
10
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
5-Azidoisoxazoles are prepared via displacement of a chlorine atom in 5-chloroisoxazoles with azide ion. These 5-azidoisoxazoles contain an unsaturated group (olefin, aldehyde, oxime or hydrazone) in the 4-position which participates during thermal decomposition of the azide. Two types of products are formed which are non-interconvertible: (i) bicyclic isoxazoles which result from direct attack of the azide or nitrene on the unsaturated group; (ii) monocyclic pyrroles and pyrazoles which result from ring opening followed by bond reorganization and subsequent ring closure. Mechanisms for the two discrete processes are discussed.