Photooxygenations of 1-naphthols: an environmentally friendly access to 1,4-naphthoquinones

Dye sensitized photooxygenations of 1-naphthols were investigated with soluble and solid-supported sensitizers and moderate to excellent yields of the corresponding 1,4-naphthoquinones were achieved in relatively short irradiation times. The mild and environmentally friendly reaction conditions made...

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Bibliographic Details
Published in:Tetrahedron 2006-02, Vol.62 (7), p.1467-1473
Main Authors: Suchard, Oliver, Kane, Ronan, Roe, Bernard J., Zimmermann, Elmar, Jung, Christian, Waske, Prashant A., Mattay, Jochen, Oelgemöller, Michael
Format: Article
Language:English
Subjects:
Green chemistry
Photochemistry
Photooxygenations
Quinones
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Summary:Dye sensitized photooxygenations of 1-naphthols were investigated with soluble and solid-supported sensitizers and moderate to excellent yields of the corresponding 1,4-naphthoquinones were achieved in relatively short irradiation times. The mild and environmentally friendly reaction conditions made this application particularly attractive for ‘Green Photochemistry’. Consequently, the photooxygenation of 1,5-dihydroxynaphthalene was studied with non-concentrated and moderately concentrated sunlight and 5-hydroxy-1,4-naphthoquinone (Juglone) was obtained in yields up to 71%. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.11.021