Tetrahedron p. 5515 - 5525 (1994)
Update date:2022-08-03
Topics:
Lamara
Redhouse
Smalley
Thompson
Unlike other aryl azides bearing electron-withdrawing ortho-substituents, o-azidobenzonitriles on photolysis in aqueous-tetrahydrofuran yield mixtures of the expected 3-cyano- and the unexpected 7-cyano-3H-azepin-2(1H)-ones. In one instance ring contraction to a 2-azabicyclo[3.2.0]hept-6-ene-3-one is noted. X-ray crystallographic data for 7-cyano- and 4-chloro-7-cyano-3H-azepin-2-one, and for the azabicycloheptenone, are presented.
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