Tetrahedron

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

S Auricchio, A Bini, E Pastormerlo, AM Truscello

Index: Auricchio, Sergio; Bini, Antonella; Pastormerlo, Eros; Truscello, Ada M. Tetrahedron, 1997 , vol. 53, # 31 p. 10911 - 10920

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Citation Number: 47

Abstract

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.