86340-09-2Relevant academic research and scientific papers
Heterocyclic Rearrangements. Synthesis and Reactivity of Oximes of Some 3-Acylisoxazoles. A Reinvestigation
Vivona, Nicolo,Macaluso, Gabriella,Frenna, Vincenzo
, p. 483 - 486 (2007/10/02)
The oximation reaction of some 3-acylisoxazoles with hydroxylamine hydrochloride and the geometry of the product oximes were reinvestigated. 3-Benzoylisoxazoles gave mixtures of (E)- and (Z)-isomers, whereas 3-acetylisoxazoles gave (E)-isomers only.The base-induced rearrangement of 3-acylisoxazole oximes to 1,2,5-oxadiazoles (furazans) was reinvestigated and was shown to depend on the geometry of the oximes since, when treated with aqueous potassium hydroxide, only (Z)-oximes readily rearranged.On the basis of our findings, some discrepancies in the literature have been corrected.
