3',3'-dichlorospiro | 58243-52-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 3',3'-dichlorospiro
• 英文别名: 2,2-Dichloro-3-(9-fluorenyl)episulfide；3',3'-dichloro-spiro[fluorene-9,2'-thiirane]；3',3'-Dichlor-spiro[fluoren-9,2'-thiiran]；3',3'-Dichlorospiro[fluorene-9,2'-thiirane]；2',2'-dichlorospiro[fluorene-9,3'-thiirane]
• CAS: 58243-52-0
• 化学式: C₁₄H₈Cl₂S
• 分子量: 279.19
• InChiKey: FCGAFHVXRWHIHK-UHFFFAOYSA-N

物化性质

• 沸点：
  436.4±45.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3',3'-dichlorospiro 以 萘烷 为溶剂， 生成 9-二氯亚甲基-9H-芴
  参考文献：
  名称：

  硫杂环丁烷中硫磺的挤出机理

  摘要：

  硫杂环丁烷热分解为烯烃不是一级反应，因此不是简单的趋化过程。

  DOI：

  10.1016/s0040-4039(00)94913-x
• 作为产物：
  描述：

  硫光气 、 9-重氮基-9H-芴 以 Petroleum ether 为溶剂， 反应 1.0h， 以61%的产率得到3',3'-dichlorospiro
  参考文献：
  名称：

  Thermal decomposition of 3',3'-dichlorospiro[fluorene-9,2'-thiirane]: kinetics and mechanism

  摘要：

  Kinetic studies on the thermal decomposition of 2,2-dichloro-3-(9-fluorenylidene)thiirane in 12 solvents have been investigated in detail. A two-term rate equation has been derived to account for the overall rate changes. Both a uni- and bimolecular ionic mechanism involving the concatenation of sulfur atoms is proposed to account for the observed kinetic behavior. Activation parameters were calculated and rationalized with respect to differences in solvation of the ground and transition states. A linear, isokinetic relationship was found indicating a similar mechanism of decomposition in these solvents. Rates of reaction were also found to be linearly correlated with dielectric constant as well as the pi* scale of Kamlet and Taft. The rate of desulfurization is decreased in the presence of acetic acid, and a radical mechanism is discounted from a rate study in the presence of radical inhibitors.

  DOI：

  10.1021/jo00068a040

文献信息

• Mechanism of sulfur extrusion from thiirane
  作者：Erich Lutz、Jean-François Biellmann

  DOI：10.1016/s0040-4039(00)94913-x

  日期：1985.1

  The thermal decomposition of thiirane to olefin is not a first order reaction, and is therefore not a simple chelotropic process.

  硫杂环丁烷热分解为烯烃不是一级反应，因此不是简单的趋化过程。
• Mechanism of sulfur extrusion in 2,2 dichloro-3-[9-fluorenyl] episulfide
  作者：Warren Chew、David N. Harpp

  DOI：10.1016/s0040-4039(00)77669-6

  日期：1992.1

  2,2 Dichloro-3-[9-fluorenyl] episulfide (2) slowly extrudes sulfur when treated thermally. The reaction generally follows unimolecular behavior but at higher concentrations in decalin, toluene and p-xylene, a bimolecular pathway is demonstrated. Kinetic and mechanistic aspects are discussed.

  当进行热处理时，2,2二氯-3- [9-芴基]环硫醚（2）缓慢挤出硫。该反应通常遵循单分子行为，但是在十氢化萘，甲苯和对二甲苯中浓度较高时，表明存在双分子途径。动力学和力学方面进行了讨论。
• Staudinger; Siegwart, Helvetica Chimica Acta, 1920, vol. 3, p. 838
  作者：Staudinger、Siegwart

  DOI：——

  日期：——
• Thermal decomposition of 3',3'-dichlorospiro[fluorene-9,2'-thiirane]: kinetics and mechanism
  作者：Warren Chew、David N. Harpp

  DOI：10.1021/jo00068a040

  日期：1993.7

  Kinetic studies on the thermal decomposition of 2,2-dichloro-3-(9-fluorenylidene)thiirane in 12 solvents have been investigated in detail. A two-term rate equation has been derived to account for the overall rate changes. Both a uni- and bimolecular ionic mechanism involving the concatenation of sulfur atoms is proposed to account for the observed kinetic behavior. Activation parameters were calculated and rationalized with respect to differences in solvation of the ground and transition states. A linear, isokinetic relationship was found indicating a similar mechanism of decomposition in these solvents. Rates of reaction were also found to be linearly correlated with dielectric constant as well as the pi* scale of Kamlet and Taft. The rate of desulfurization is decreased in the presence of acetic acid, and a radical mechanism is discounted from a rate study in the presence of radical inhibitors.