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Issue 0, 1972
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Reductive and oxidative cleavage of 5-phenyl-Δ2-isoxazoline-3-carboxylic acid

Abstract

The reductive cleavage of 5-phenyl-Δ2-isoxazoline-3-carboxylic acid (II; R = H) with zinc in acetic acid to give 4-phenyl-2-acetamido-γ-butyrolactone (III) is described. Oxidative fragmentation of the peroxy-esters t-butyl 5-phenyl-Δ2-isoxazoline-3-peroxycarboxylate (II; R = OBut) and t-butyl 5-phenylisoxazole-3-peroxycarboxylate (V; R = OBut) parallels the mass spectral fragmentation, to give benzaldehyde and 3-hydroxy-3-phenyl-propionitrile (VI), and 5-phenylisoxazole-3-carboxylic acid (V; R = H), respectively.

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Article type: Paper
DOI: 10.1039/P19720000437
Citation: J. Chem. Soc., Perkin Trans. 1, 1972,0, 437-443
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    Reductive and oxidative cleavage of 5-phenyl-Δ2-isoxazoline-3-carboxylic acid

    G. S. King, P. D. Magnus and H. S. Rzepa, J. Chem. Soc., Perkin Trans. 1, 1972, 0, 437
    DOI: 10.1039/P19720000437

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