171003-95-5Relevant academic research and scientific papers
Rearrangements of 5-Azidoisoxazoles
Anderson, David J.,Muchmore, Christine R.
, p. 1189 - 1196 (2007/10/02)
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.
