Stereochemistry in the conversion of phenyldiazomethane into stilbenes and spirooxetanes caused by tetrahalogenated 1,4-benzoquinones. Effects of halogen substituents.
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概要
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Reaction of phenyldiazomethane (<B>1</B>) with tetrafluoro-1,4-benzoquinone (<B>2a</B>) gave isomeric mixtures of stilbenes (<B>3</B>, cis/trans=4.7) and spirooxetanes (<B>4a</B>, cis/trans=1.1) via zwitterion intermediates. Similarly, tetrabromo-1,4-benzoquinone (<B>2c</B>) provided <B>3</B> and spirooxetane (<B>4c</B>); however, the cis/trans ratio of <B>3</B> dropped to 2.3 and <B>4c</B> was solely the trans isomer. On the other hand, reaction with tetraiodo-1,4-benzoquinone (<B>2d</B>) afforded no spirooxetane and gave a further reduced isomer ratio of <B>3</B> of 1.9.
- 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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