5-(4-hydroxy-3,5-di-fluorophenyl)thianthreniumyl perchlorate | 139656-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二硫类化合物
• 英文名称: 5-(4-hydroxy-3,5-di-fluorophenyl)thianthreniumyl perchlorate
• CAS: 139656-65-8
• 化学式: C₁₈H₁₁F₂OS₂*ClO₄
• 分子量: 444.864
• InChiKey: ITGOIPJVMMSMGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• sp3杂化的碳原子比例：
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反应信息

• 作为产物：
  描述：

  2,6-二氟苯酚 、 thianthrene cation radical perchlorate 以 乙腈 为溶剂， 反应 48.0h， 以53%的产率得到5-(4-hydroxy-3,5-di-fluorophenyl)thianthreniumyl perchlorate
  参考文献：
  名称：

  Reactions of phenols with thianthrene cation radical

  摘要：

  The phenols 2-R1-6-R2-phenol 1a-g in which R1 = R2 = tert-butyl, methyl, isopropyl, Cl, Br, F, and H reacted with thianthrene cation radical perchlorate (Th.+ClO4-) to give 5-(4-hydroxyaryl)thianthreniumyl perchlorates 2a-g in good yield. o-Allylphenol (1i) behaved similarly. o-tert-Butylphenol (1h) gave both 5-(3-tert-butyl-4-hydroxyphenyl)thianthreniumyl perchlorate (2h) and a quinonoidal perchlorate (3), namely, 5-(3-thianthreniumyl-5-tert-butyl-6-oxo-2,4-cyclohexadien-1-ylidene)-5,5-dihydrothianthrene perchlorate. The 2,6-di-tert-butyl-4-R3-phenols 4a-c, R3 = tert-butyl, methoxy, and methyl, reacted with Th.+ClO4- in nitrile solvents (RCN) to give 2-R-5-R3-7-tert-butylbenzoxazoles 5a-e. The tert-butyl group that was displaced by RCN in forming 5 was converted into t-BuNHCOR (8), tert-butyl alcohol, and isobutene. In contrast, 2-tert-butyl-4,6-dimethylphenol (9) gave, in CH3CN, 4-tert-butyl-2,5,7-trimethylbenzoxazole (11), that is, with migration of the displaced tert-butyl group. The reactions of 4-tert-butylphenol (14) and 2,4-di-tert-butylphenol (17) are also described.

  DOI：

  10.1021/jo00035a031