Rearrangements vs Fragmentations in the Dye-sensitized Photooxygenation of N-Aryl α-Furanamides

Author(s): Maria R. Iesce, Flavio Cermola, Rosalia Sferruzza, Marina DellaGreca.

Journal Name: Current Organic Chemistry

Volume 20 , Issue 20 , 2016

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Abstract:

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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Article Details

VOLUME: 20
ISSUE: 20
Year: 2016
Page: [2117 - 2124]
Pages: 8
DOI: 10.2174/1385272820666160505123742
Price: $58

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