89903-25-3Relevant academic research and scientific papers
X=Y-ZH Systems as Potential 1,3-Dipoles. Part 2. Oxime cycloadditions: formation of 2:1 Adducts
Grigg, Ronald,Jordan, Maurice,Tangthongkum, Aant,Einstein, Frederick W. B.,Jones, Terry
, p. 47 - 57 (2007/10/02)
Cycloaddition of aldehyde and ketone oximes are shown to give mixtures of all possible isoxazolidine regioisomers and stereoisomers.The products are 2:1 adducts with the second molecule of the dipolarophile attached to the isoxazolidine N-atom.The stereochemistry of the major isomer from benzaldehyde oxime and acrylonitrile was established by an X-ray crystal structure analysis.The cycloaddition is shown to be weakly catalysed by 2,4-dinitrophenol and to proceed best in acetonitrile.More polar solvents slightly favour the 5-isoxazolidine regioisomer.The mechanism of the reaction is discussed.
