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DOI: 10.1055/s-0040-1719903
Hydrogen-Bonded Xanthones as Potential UV Absorbers: The Synthesis of Xanthones from Bio-Renewable Cardanol Utilizing a Ceric Ammonium Sulfate (CAS)-Mediated Oxidation Reaction
The authors would like to thank the South African National Research Foundation (NRF) under the German/South Africa Research Cooperation for funding of the project.
Abstract
The synthesis of hydrogen-bonded xanthones by using biorenewable hydrogenated cardanol (3-pentadecylphenol) is described. Hydrogenated cardanol was initially converted into various hydroxybenzophenones. These benzophenones were converted into xanthones by utilizing an oxidative ceric ammonium sulfate-mediated reaction. A subsequent ruthenium-mediated late-stage oxidation of the xanthones provided hydrogen-bonded xanthones, which displayed good UVA and UVB absorbing properties.
Key words
cardanols - benzophenones - ceric ammonium sulfate - oxidative addition - xanthones - UV absorbersSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719903.
- Supporting Information
- Mass spectra
Publication History
Received: 11 January 2022
Accepted after revision: 28 January 2022
Article published online:
24 February 2022
© 2022. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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Other related oxidative cyclization reactions have been reported; for an example of a phenol-mediated oxidative cyclization with Ag2CO3, see:
For a DDQ oxidation of 1,4-hydroquinones to afford spiro-type compounds, see ref. 5a and: