di-9-fluorenyl sulfoxide | 132020-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: di-9-fluorenyl sulfoxide
• 英文别名: di-fluoren-9-yl sulfoxide；Di-fluoren-9-yl-sulfoxid；9-(9H-fluoren-9-ylsulfinyl)-9H-fluorene
• CAS: 132020-45-2
• 化学式: C₂₆H₁₈OS
• 分子量: 378.494
• InChiKey: XWVALSQNTOZULT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  di-9-fluorenyl sulfoxide 在 双氧水 作用下， 生成 di-fluoren-9-yl sulfone
  参考文献：
  名称：

  Courtot; Kozertchouk, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1944, vol. 218, p. 973

  摘要：

  DOI：
• 作为产物：
  描述：

  di-9-fluorenyl sulfide 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以60%的产率得到di-9-fluorenyl sulfoxide
  参考文献：
  名称：

  Studies of reactions leading to sulfine formation. 6. Base-catalyzed decomposition of di-9-fluorenyl sulfoxide

  摘要：

  When treated with CH3ONa in CH3OH-CH2Cl2, di-9-fluorenyl sulfoxide (3) undergoes elimination readily to afford 9-thiofluorenone S-oxide (4) and fluorene (eq 2). Comparison of the rate of the elimination to the rate of disappearance in the presence of CD3OD of the H-1 NMR signal for the 9-H in 3 shows that the mechanism of this sulfine-forming elimination is (E1cB)rev, the rate of cleavage of the intermediate alpha-sulfinyl carbanion 7 to give 4 and a 9-fluorenyl carbanion being over 100 times slower than the rate at which 7 is protonated to regenerate 3. The (E1cB)rev behavior of this elimination is contrasted with the (E1cB)rev/(E1cB)irrev borderline behavior of the elimination of diarylmethyl (arylmethyl)sulfonyl sulfoxides 1, 2 and a reason for this at first sight unexpected difference in behavior is presented.

  DOI：

  10.1021/jo00004a018

文献信息

• Studies of reactions leading to sulfine formation. 6. Base-catalyzed decomposition of di-9-fluorenyl sulfoxide
  作者：John L. Kice、Lidia Kupczyk-Subotkowska

  DOI：10.1021/jo00004a018

  日期：1991.2

  When treated with CH3ONa in CH3OH-CH2Cl2, di-9-fluorenyl sulfoxide (3) undergoes elimination readily to afford 9-thiofluorenone S-oxide (4) and fluorene (eq 2). Comparison of the rate of the elimination to the rate of disappearance in the presence of CD3OD of the H-1 NMR signal for the 9-H in 3 shows that the mechanism of this sulfine-forming elimination is (E1cB)rev, the rate of cleavage of the intermediate alpha-sulfinyl carbanion 7 to give 4 and a 9-fluorenyl carbanion being over 100 times slower than the rate at which 7 is protonated to regenerate 3. The (E1cB)rev behavior of this elimination is contrasted with the (E1cB)rev/(E1cB)irrev borderline behavior of the elimination of diarylmethyl (arylmethyl)sulfonyl sulfoxides 1, 2 and a reason for this at first sight unexpected difference in behavior is presented.
• Courtot; Kozertchouk, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1944, vol. 218, p. 973
  作者：Courtot、Kozertchouk

  DOI：——

  日期：——