Ceric ammonium sulfate (CAS) mediated oxidations of benzophenones possessing a phenolic substituent for the synthesis of xanthones and related products.

Author(s) Dam, J.; Bode, M.L.; de Koning, C.B.
Journal J Org Chem
Date Published 2018 Dec 05

Work previously published by our group described novel methodology for the synthesis of xanthones and related products from phenolic benzophenones in a reaction mediated by ceric ammonium sulfate (CAS). In this paper we further explore this novel reaction by subjecting an additional set of phenolic benzophenones to CAS to afford a range of compounds, including xanthones, 9H-xanthen-2,9(4aH)-diones, 3H-spiro[benzofuran-2,1'-cyclohexa[2,5]diene]-3,4'-diones and biaryl compounds. Based on these results, greater insight into the reaction mechanism has been gained. In addition, the conversion of the synthesized xanthen-2,9(4aH)-diones to xanthones by treatment with sodium dithionite is described.

DOI 10.1021/acs.joc.8b02503
ISSN 1520-6904
Citation J Org Chem. 2018.

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