The Cerium(IV) Ammonium Nitrate Oxidation of 5-Hydroxy-2-methoxytropone to Bitropolonyl Derivatives and One-Step Synthesis of 3-Methoxy-p-tropoquinone

Article abstract of DOI:10.1246/bcsj.59.511

Unlike the benzenoid equivalent, p-methoxyphenol, the cerium(IV) ammonium nitrate (CAN)-oxidation of 5-hydroxy-2-methoxytropone gave C-C coupling products.On the other hand, either by thallium(III) nitrate (TTN) or CAN at 50 deg C, 5-hydroxytropolone, a free tropolone, gave 3-methoxy-p-tropoquinone together with p-tropoquinone and 8-oxabicyclo<3.2.1>octenone derivatives, but no dimeric product.