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Formation of Phenalenone Skeleton by an Unusual Rearrangement Reaction
Organic Letters ( IF 4.9 ) Pub Date : 2017-08-28 00:00:00 , DOI: 10.1021/acs.orglett.7b02305 Sayaka Sasaki 1 , Eriko Azuma 1 , Takahiro Sasamori 2 , Norihiro Tokitoh 2 , Kouji Kuramochi 3 , Kazunori Tsubaki 1
Organic Letters ( IF 4.9 ) Pub Date : 2017-08-28 00:00:00 , DOI: 10.1021/acs.orglett.7b02305 Sayaka Sasaki 1 , Eriko Azuma 1 , Takahiro Sasamori 2 , Norihiro Tokitoh 2 , Kouji Kuramochi 3 , Kazunori Tsubaki 1
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The frame rearrangement reaction of dinaphthyl ketones, possessing hydroxy groups at appropriate positions, into phenalenone derivatives under acidic conditions was discovered serendipitously. Although this rearrangement had limited scope, its mechanism was unusual, involving the division of naphthalene rings into one phenalenone ring and one benzene ring. The reaction mechanism was elucidated by direct determination of intermediate structures using 1H NMR measurements. The generated phenalenones are expected to be key intermediates toward natural products and functional materials.
中文翻译：
通过异常重排反应形成苯肾上腺素骨架
偶然发现了在酸性条件下在适当位置具有羟基的二萘甲酮向苯丙烯酮衍生物的骨架重排反应。尽管这种重排的范围有限，但是其机理却很不寻常，涉及将萘环分为一个菲拉烯酮环和一个苯环。通过使用1 H NMR测量直接确定中间结构来阐明反应机理。预计生成的非对苯二酚是天然产物和功能材料的关键中间体。
更新日期：2017-08-28
中文翻译：
通过异常重排反应形成苯肾上腺素骨架
偶然发现了在酸性条件下在适当位置具有羟基的二萘甲酮向苯丙烯酮衍生物的骨架重排反应。尽管这种重排的范围有限，但是其机理却很不寻常，涉及将萘环分为一个菲拉烯酮环和一个苯环。通过使用1 H NMR测量直接确定中间结构来阐明反应机理。预计生成的非对苯二酚是天然产物和功能材料的关键中间体。
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