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  • CAN-mediated oxidations for the synthesis of xanthones and related products.

CAN-mediated oxidations for the synthesis of xanthones and related products.

The Journal of organic chemistry (2010-11-23)
Myron M Johnson, Jeremy M Naidoo, Manuel A Fernandes, Edwin M Mmutlane, Willem A L van Otterlo, Charles B de Koning
ABSTRACT

Reaction of (2,4,5-trimethoxyphenyl)(2-hydroxyphenyl)methanone with ceric ammonium nitrate furnished the xanthone, 2,3-dimethoxy-9H-xanthen-9-one. Under the same conditions the related (1,4-dimethoxynaphthalen-2-yl)(2-hydroxyphenyl)methanone resulted in the formation of 12a-methoxy-5H-benzo[c]xanthenes 5,7(12aH)-dione. Other examples of this novel transformation are also outlined.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ammonium cerium(IV) nitrate, ≥99.99% trace metals basis
Sigma-Aldrich
Ammonium cerium(IV) nitrate, JIS special grade, ≥95.0%
Sigma-Aldrich
Ammonium cerium(IV) nitrate, ≥98% (titration)
Sigma-Aldrich
Ammonium cerium(IV) nitrate, ACS reagent, ≥98.5%
Sigma-Aldrich
Ammonium cerium(IV) nitrate, puriss. p.a., ACS reagent, ≥98.5% (RT)