Photooxygenation of Electron-Poor Trisubstituted Furans: Novel Aspects and Applications

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

Journal Name: Current Organic Chemistry

Volume 19 , Issue 5 , 2015

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Abstract:

Photooxygenation of titled furans followed by reduction gives unsaturated 4-oxoaldehydes quantitatively. Some derivatives cyclize under slightly acid conditions or by silica gel to unusual 5,6- dioxabicyclo[2.1.1]hexenes and/or 5H-furanones. Under appropriate basic conditions 4-oxocarboxylic acids or their ring-tautomers 5-hydroxyfuranones are chemoselectively obtained in almost quantitative yields. All the procedures are one-pot and occur stereoselectively. Due to the electron-poor substituents alternative non-photochemical oxidative methods fail or give not cleanly reaction mixtures.

Keywords: 4-oxo acids, 4-oxoaldehydes, base treatment, furan endoperoxides, reduction, singlet oxygen.

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Article Details

VOLUME: 19
ISSUE: 5
Year: 2015
Page: [475 - 480]
Pages: 6
DOI: 10.2174/1385272819666150122001332
Price: $58

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