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Oxidation of 2,2’-Dihydroxy-3,3’-di-tert-buty-5,5’-dimethoxyl-biphenyl to 3,3’-Di-tert-butylbiphenyl-2,5,2’,5’-diquinone with Copper(Ⅱ)Chloride as Catalyst:Synthesis,Structure and Spectral Properties of Diquinone

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【作者】 李俊霞； 王建革； 黄唯平；

【Author】 LI Jun-Xiaa② WANG Jian-Gea HUANG Wei-Pingb a(College of Chemistry and Chemical Engineering,Luoyang Normal University,Luoyang,Henan 471022,China)b(College of Chemistry,Nankai University,Tianjin 300071,China)

【机构】 College of Chemistry and Chemical Engineering,Luoyang Normal University,Luoyang； College of Chemistry,Nankai University；

【摘要】 Use of free air as oxidant and copper(II)chloride as catalyst,3,3’-di-tert-butylbi-phenyl-2,5,2’,5’-diquinone(BBDQ)was prepared via catalytic oxidation of 2,2’-dihydroxy-3,3’-di-tert-butyl-5,5’-dimethoxy-biphenyl(di-BHA).The yield of reaction attained 95% and the selectivity for BBDQ was 100%.The single-crystal X-ray diffraction analysis reveals that the dihedral angle between two rings(benzene rings for di-BHA and quinone rings for BBDQ)changes from 89.8 to 45.3o,indicating the steric hindrance effects of methyl disappear in the oxidation process.The crystal structures of di-BHA and BBDQ are further confirmed by their spectral characterizations.The probable mechanism for this oxidation process is also discussed.

【Abstract】 Use of free air as oxidant and copper(II)chloride as catalyst,3,3’-di-tert-butylbi-phenyl-2,5,2’,5’-diquinone(BBDQ)was prepared via catalytic oxidation of 2,2’-dihydroxy-3,3’-di-tert-butyl-5,5’-dimethoxy-biphenyl(di-BHA).The yield of reaction attained 95% and the selectivity for BBDQ was 100%.The single-crystal X-ray diffraction analysis reveals that the dihedral angle between two rings(benzene rings for di-BHA and quinone rings for BBDQ)changes from 89.8 to 45.3o,indicating the steric hindrance effects of methyl disappear in the oxidation process.The crystal structures of di-BHA and BBDQ are further confirmed by their spectral characterizations.The probable mechanism for this oxidation process is also discussed.

【关键词】 catalytic oxidation； 3； 3’-di-tert-butylbiphenyl-2； 5； 2’； 5’-diquinone； 2； 2’-dihydroxy-3； 3’-di-tert-butyl-5； 5’-dimethoxybiphenyl； copper(II)chloride；
【Key words】 catalytic oxidation； 3； 3’-di-tert-butylbiphenyl-2； 5； 2’； 5’-diquinone； 2； 2’-dihydroxy-3； 3’-di-tert-butyl-5； 5’-dimethoxybiphenyl； copper(II)chloride；
【基金】 supported by the 973 Program (2005CB623607);the National Natural Science Foundation of China (No.20771061);the scientific program 2008BAE64B09
  • 【文献出处】 结构化学 ,Chinese Journal of Structural Chemistry , 编辑部邮箱 ,2011年10期
  • 【分类号】O643.32
  • 【下载频次】14
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