The reaction of variously N-substituted α-furanamides with singlet oxygen has
been examined. In addition to the expected fragmentation products the reaction affords rearranged
5-hydroxy- and 5-aryloxy-2(5H)-furanones. Products distribution depends on diverse
factors: the presence of α-hydrogen, the presence of the amidic group, the nature and the
number of nitrogen substituents. The rearrangement to 5-aryloxy-2(5H)-furanones is unreported.
Keywords: Photooxygenation, furanamides, furanones, N-O transfer, singlet oxygen, γ-Hydroxybutenolide.
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