Journal of the Chemical Society. Perkin transactions I p. 47 - 57 (1984)
Update date:2022-07-29
Topics:
Grigg, Ronald
Jordan, Maurice
Tangthongkum, Aant
Einstein, Frederick W. B.
Jones, Terry
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.
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Doi:10.1246/bcsj.57.611
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