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Rearrangements of 5‐azidoisoxazoles
Author(s) -
Anderson David J.,
Muchmore Christine R.
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320416
Subject(s) - chemistry , nitrene , azide , ring (chemistry) , hydrazone , oxime , thermal decomposition , bicyclic molecule , aldehyde , olefin fiber , medicinal chemistry , double bond , carbonyl group , stereochemistry , organic chemistry , catalysis
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.