Addition of diphenyldiazomethane to unsubstituted and chloro-substituted 1,4-benzoquinones. Effects of chloro substituents on the addition modes.
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概要
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Unsubstituted 1,4-benzoquinone (<B>1a</B>) reacted with diphenyldiazomethane (DDM) at the C=C double bonds to give dihydroxy-3<I>H</I>-indazole (<B>2a</B>) and its benzhydryl ether (<B>3a</B>) together with benzodipyrazole derivative (<B>4a</B>). Similarly, reactions of 2-chloro- and 2,3-dichloro-1,4-benzoquinones (<B>1b</B> and <B>1c</B>) with DDM yielded the corresponding dihydroxy-3<I>H</I>-indazoles (<B>2b</B>, <B>2b</B>′, and <B>2c</B>) and their benzhydryl ethers (<B>3b</B>, <B>3b</B>′, and <B>3c</B>) along with 5–13% benzophenone (<B>6</B>). On the other hand, reaction of 2,6-dichloro-1,4-benzoquinone (<B>1e</B>) with DDM gave bicyclic <B>5e</B> and tricyclic diones (<B>7e</B>), together with benzophenone dimethyl acetal (<B>9</B>) in the presence of added methanol. In the same conditions, 2,3,5-trichloro-1,4-benzoquinone (<B>1f</B>) provided bicyclic dione (<B>5f</B>) and <B>9</B>. Formation of <B>6</B> and <B>9</B> was interpreted as arising from the hydrolysis and methanolysis of the 1:1 betaine intermediates given by the addition of DDM to the quinonoid C=O double bonds. The C=O addition increased with increasing chlorine substituents.
- 公益社団法人 日本化学会の論文
著者
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Oshima Takumi
Institute Of Chemistry College Of General Education Osaka University
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Nagai Toshikazu
Institute Of Chemistry College Of General Education Osaka University
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