Reaction of azomethine N-oxides. III. Reactions of some azomethine N-oxides with fluoranil, phenyl vinyl sulfone, and .BETA.-nitrostyrene.
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Isomerization of 3<I>H</I>-indole 1-oxides in the presence of tetrafluoro-2,5-cyclohexadiene-1,4-dione (fluoranil) to the thermodynamically more stable lactams was found to proceed via formation of charge-transfer complexes. However, addition of fluoranil to some open chain nitrones did not give the corresponding amides. Both electron-deficient β-nitrostyrene and phenyl vinyl sulfone did not form charge-transfer complexes with nitrones, but instead they undergo 1,3-dipolar cycloaddition giving 4- or 5-substituted isoxazolidines.
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