Issue 0, 1984

X[double bond, length half m-dash]Y–ZH systems as potential 1,3-dipoles. Part 2. Oxime cycloadditions: formation of 2 : 1 adducts

Abstract

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 di-polarophile 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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1984, 47-57

X[double bond, length half m-dash]Y–ZH systems as potential 1,3-dipoles. Part 2. Oxime cycloadditions: formation of 2 : 1 adducts

R. Grigg, M. Jordan, A. Tangthongkum, F. W. B. Einstein and T. Jones, J. Chem. Soc., Perkin Trans. 1, 1984, 47 DOI: 10.1039/P19840000047

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements