Iron dichloride induced isomerization or reductive cleavage of isoxazoles: A facile synthesis of 2-carboxy-azirines

Article abstract of DOI:10.1016/S0040-4020(97)00696-0

5-Alkoxy-isoxazoles and N,N-disubstituted-5-isoxazolamines were found to isomerize to azirine derivatives by the use of iron dichloride as catalyst. On the contrary 5-alkyl- and 5-aryl-isoxazoles in the presence of the same salt, undergo reductive cleavage to enaminoketones. A common reaction intermediate is proposed.