Preparation of polyacetoxytropones and polyhydroxytropolones by acetolysis and hydrolysis of halotroponoids by acetyl trifluoroacetate with exhaustive displacement of halogens on the tropone ring. Predominant formation of reductive acetolysates from fully

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概要

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• Di-, tri-, and tetrahydroxytropolones were prepared in good yields by the acetolysis of corresponding halotropones or polyhalotropolones with acetyl trifluoroacetate followed by acetic acid hydrolysis. However, using the same treatment to obtain hexaacetoxytropone with fully substituted acetoxyhalotropones predominantly yielded fewer substituted acetoxytropones than expected; the mechanism of formation was shown to involve an acetic acid-mediated reduction of intermediary formed acetoxy-<I>p</I>-tropoquinone equivalents. A couple of 2,7-unsubstituted 3,4-diacetoxytropones were deduced to have cyclized 1,3-dioxole structures, 2-acetoxy-2-methyl-5<I>H</I>-cyclohepta-1,3-dioxol-5-ones. An acetolysis of the brominated 5-isopropyltropolones furnished an acetylated by-product, 2,3,7-triacetoxy-5-(1,1-dimethyl-2-oxopropyl)tropone, which might be formed by the acylation of an intermediate, 3,4,5,6-tetraacetoxy-8,8-dimethylheptafulvene.

• 公益社団法人 日本化学会の論文

著者

• Mori Akira

  Research Department Of Mechanical Control Research Center Research Division Komatsu Ltd.

• Takeshita Hitoshi

  Research Institute of Industrial Science, 86, Kyushu University

• Kusaba Tomoyuki

  Graduate School of Engineering Sciences, 39, Kyushu University

• Watanabe Hiroyasu

  Graduate School of Engineering Sciences, 39, Kyushu University

• Takeshita Hitoshi

  Research Institute of Industrial Sciece, 86, Kyushu University

関連論文

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• Preparation of polyacetoxytropones and polyhydroxytropolones by acetolysis and hydrolysis of halotroponoids by acetyl trifluoroacetate with exhaustive displacement of halogens on the tropone ring. Predominant formation of reductive acetolysates from fully
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