Synthesis of decachloro-4-allylidenecyclopentene and its chemistry.

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概要

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• Decachloro-4-allylidenecyclopentene (<B>6</B>) was synthesized by the reaction of pentachlorocyclopentadiene with hexachloropropene in the presence of anhydrous aluminium chloride. Hexachloro-2-allylidene-4-cyclopentene-1,3-dione (<B>11</B>), prepared from <B>6</B> by treatment with coned nitric acid, cyclized to hexachloro-2,5-dihydrocyclopenta[<I>b</I>]pyran-5-one (<B>14</B>) on heating. In a solvent such as acetone and acetonitrile, <B>4</B> rearranged to hexachloro-2,5-dihydrocyclopenta[<I>b</I>]pyran-2-one (<B>18</B>) at room temperature. The mechanism of this rearrangement is discussed. Hydrolysis of <B>14</B> by 90% sulfuric acid afforded tetrachloro-2,5-dihydrocyclopenta[<I>b</I>]pyran-2,5-dione (<B>15</B>), which was obtained directly from <B>6</B> by treatment with sulfuric acid. The reactions of <B>11</B> with anhydrous methanol, and of <B>15</B> with diazomethane were investigated.

• 公益社団法人 日本化学会の論文

著者

• Kusuda Kousuke

  Research Institute for Atomic Energy, Osaka City University

• Roedig Alfred

  Institut für Organische Chemie, Universität Würzburg

関連論文

• Synthesis of decachloro-4-allylidenecyclopentene and its chemistry.

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