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首页> 外文期刊>Chemistry: A European journal >Domino Friedel-crafts-type cyclizations of difluoroalkenes promoted by the α-cation-stabilizing effect of fluorine: An efficient method for synthesizing angular PAHs
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Domino Friedel-crafts-type cyclizations of difluoroalkenes promoted by the α-cation-stabilizing effect of fluorine: An efficient method for synthesizing angular PAHs

机译：Domino Friedel-Crafts型二氟烯烃的旋转式环化促进氟的α-阳离子稳定作用：合成角度PAHs的有效方法

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摘要

In order to synthesize polycyclic aromatic hydrocarbons with nonlinear arrangements (angular PAHs), acid-promoted domino cyclizations of 1,1-difluoroalk-1-enes and 1,1-difluoroalka-1,3-dienes were studied. 1,1-Difluoroalkenes, each bearing two aryl substituents, were regioselectively protonated with FSO_3H·SbF_5 to generate fluorine-stabilized carbocations, which readily underwent domino Friedel-Crafts-type cyclizations to give carbocycles based on 6/n/m/6 ring systems (n,m=5-7) in good to high yields. Protonation of 1,1-difluoroalka-1,3- dienes took place at their electron-rich methylene (CH_2) carbon atoms in the presence of milder acids such as camphorsulfonic acid and trifluoromethanesulfonic acid. Domino cyclizations of the resulting fluorine-stabilized allylic carbocations afford carbocycles based on 6/6/6/6 or 6/6/5/6 ring systems in high yields.
机译：为了合成具有非线性布置（角度Pahs）的多环芳烃，研究了1,1-二氟烷基-1-烯和1,1-二氟烷基-1,3-二烯的酸促进的多米诺环化。 用FSO_3H·SBF_5的含有两个芳基取代基的每种轴承两种芳基取代基得到含氟稳定的碳酸碳，其易于接受Domino Friedel-Crafics型环化，以基于6 / N / M / 6环系统提供碳缩乳。 （n，m = 5-7）良好的高产率。 在富含富含樟脑酸和三氟甲磺酸的情况下，在其电子富含电子亚甲基（CH_2）碳原子的碳原子上进行了1,1-二氟烷烃-1,3-二烯的质子化。 由此产生的氟稳定的烯丙基碳化碳的多米诺芳基环化提供基于6/6/6/6/6/6/6/5/6环体系的碳缩乳，高产率。

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  • 来源
    《Chemistry: A European journal》 |2011年第43期|共11页
  • 作者

    Fuchibe K.; Jyono H.; Fujiwara M.; Kudo T.; Yokota M.; Ichikawa J.;

  • 作者单位

    Department of Chemistry Graduate School of Pure and Applied Sciences University of Tsukuba Tsukuba 305-8571 Japan;

    Department of Applied Chemistry Kyushu Institute of Technology Kitakyushu 804-8550 Japan;

    Department of Applied Chemistry Kyushu Institute of Technology Kitakyushu 804-8550 Japan;

    Department of Applied Chemistry Kyushu Institute of Technology Kitakyushu 804-8550 Japan;

    Department of Chemistry Graduate School of Science University of Tokyo Hongo Bunkyo-ku Tokyo 113-0033 Japan;

    Department of Chemistry Graduate School of Pure and Applied Sciences University of Tsukuba Tsukuba 305-8571 Japan;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 应用化学;
  • 关键词

    carbocations; domino reactions; fluorine; helicenes; PAHs;

    机译：carbocations;多米诺反应;氟;直升机;PAHS;

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