Reactions of aryldiazomethanes with chloranil.
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概要
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The reactions of several aryldiazomethanes (<B>1a</B>: <I>p</I>-tolyl; <B>1b</B>: phenyl; <B>1c</B>: <I>p</I>-chlorophenyl) with chloranil gave stilbenes (<B>3</B>) and spiro-oxetanes (<B>4</B>) at 20 °C in tetrahydrofuran or 1,2-dichloroethane. The isomer ratios of <B>3</B> were <I>ca.</I> 2 to 3:1 in favor of <I>cis</I>, depending on the solvents and on the substituents of <B>1</B>. In the case of <B>4</B>, however, stable <I>trans</I>-isomers were selectively formed. On the other hand, the presence of added CH<SUB>3</SUB>OH suppressed the formations of <B>3</B> and <B>4</B> and, instead, induced redox reactions giving α,α-dimethoxyarylmethanes and tetrachlorohydroquinone (<B>6</B>). In these redox reactions, the acid decompositions of <B>1</B> with <B>6</B> were also found. However, the presence of CF<SUB>3</SUB>CH<SUB>2</SUB>OH allowed the formation of considerable amount of <B>3</B> and <B>4</B>, along with the redox products. The mechanism of these reactions will be discussed.
- 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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Nagai Toshikazu
Institute Of Chemistry College Of General Education Osaka University
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