Addition of 9-diazofluorene to unsubstituted and chloro-substituted 1,4-benzoquinones. A comparison with the addition of diphenyldiazomethane.
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概要
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Unsubstituted 1,4-benzoquinone (<B>1a</B>) reacted at the C=C double bond with 9-diazofluorene (9-DF) to give norcarene dione <B>2a</B> and 4,7-dihydroxy-3<I>H</I>-indazole <B>4a</B>. Similarly, the reaction of 2-chloro-1,4-benzoquinone (<B>1b</B>) with 9-DF yielded norcarene dione <B>2b</B> and 4,7-dihydroxy-3<I>H</I>-indazole <B>4b</B>, together with tricyclic dione <B>3b</B>. 2,3-dichloro-1,4-benzoquinone (<B>1c</B>) and 9-DF produced norcarene dione <B>2c</B>, 4,7-dihydroxy-3<I>H</I>-indazole <B>4c</B>, and its fluorenyl ether <B>5c</B>. Reactions of 2,5- and 2,6-dichloro- and trichloro-1,4-benzoquinones (<B>1d</B>, <B>1e</B>, and <B>1f</B>) with 9-DF provided norcarene diones <B>2d</B>, <B>2e</B>, and <B>2f</B> and tricyclic diones <B>3d</B> and <B>3e</B>, respectively. On the other hand, tetrachloro-1,4-benzoquinone (<B>1g</B>) converted 9-DF into 9,9′-bifluorenylidene possibly via a 1:1 betaine intermediate arising from the C=O double bond addition. These results were markedly different from those of the previous diphenyldiazomethane reactions and are discussed in terms of structural changes of these diazoalkanes.
- 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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- Kinetic solvent effects in the decomposition of diphenyldiazomethane with chloranil and 2,5-dichloro-p-benzoquinone.
- The reactions of a variety of diazo compounds with sulfur dioxide in ethanol.
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