Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Cerium(IV) Ammonium Nitrate Oxidation of 5-Hydroxy-2-methoxytropone to Bitropolonyl Derivatives and One-Step Synthesis of 3-Methoxy-p-tropoquinone
Akira MoriYasutoshi IsayamaHitoshi Takeshita
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1986 Volume 59 Issue 2 Pages 511-514

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Abstract

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 °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.

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