The Bromination of 2-Methoxytropone and Its Bromo Derivatives

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概要

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• The reaction of 2-methoxytropone and its bromo derivatives with bromine was examined in various solvents. The treatment of 2-methoxytropone or 5-bromo-2-methoxytropone with bromine in methanol gave an addition product, 2,6-dibromo-7,7-dimethoxy- (II) or 2,4,6-tribromo-7,7-dimethoxy-2,4-cycloheptadien-1-one (XIV) respectively, together with the substitution products. On the contrary, the treatment of 2-methoxytropone with bromine in anhydrous ethanol, chloroform, or carbon tetrachloride gave a reddish complex compound. In aqueous ethanol or acetic acid, however, it gave 3,5,7-tribromotropolone. A possible reaction mechanism involving the nucleophilic attack of a methanol molecule on 2-methoxytropones at the 2-position is presented to account for the formation of the addition products.

• 公益社団法人 日本化学会の論文

著者

• Yasunami Masafumi

  Department Of Chemistry Faculty Of Science Tohoku University

• Takase Kahei

  Department Of Chemistry Faculty Of Science Tohoku University

• Nozoe Tetsuo

  Department of Chemistry Faculty of Science Tohoku University

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