sodium 1-chloro-2,2,2-trifluoroethanesulfinate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: sodium 1-chloro-2,2,2-trifluoroethanesulfinate
• 英文别名: Sodium 1-chloro-2,2,2-trifluoroethane-1-sulfinate；sodium;1-chloro-2,2,2-trifluoroethanesulfinate
• 化学式: C₂HClF₃O₂S*Na
• 分子量: 204.533
• InChiKey: KPVGMYBZJHWJDP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.0
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  sodium 1-chloro-2,2,2-trifluoroethanesulfinate 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到1-chloro-2,2,2-trifluoroethanesulfonyl chloride
  参考文献：
  名称：

  1-氯-2,2,2-三氟乙磺酰氯与1,2,2,2-四氟乙磺酰氟与胺的反应中卤素迁移与卤化氢消除的关系：理论和实验研究

  摘要：

  已经提出了一种简单且有用的方法来制备1-氯-2,2,2-三氟乙磺酸磺酰氯。通过1-氯-2，2，2-三氟乙磺酰氯的氨解，氯迁移进行，形成1，1-二氯-2，2，2-三氟乙亚磺酸的相应盐。已经使用量子化学（DFT和MP2）方法研究了该过程以及替代反应，即消除卤化氢。如计算数据所示，中间形成的阴离子经由三元环状过渡态经历分子内氯迁移。后者的特征在于低的活化能（ΔE  ＝ 27.0kcal / mol）。在1,2,2,2-四氟乙硫磺酰氟的情况下，活化的障碍要高得多（ΔE ＝ 41.6kcal / mol）。1,1-二氯-2,2,2-三氟乙磺酸亚磺酸和1,1,2,2,2-五氟乙亚磺酸阴离子的结构可以认为是全卤代烷基阴离子与SO 2的供体-受体配合物。

  DOI：

  10.1016/j.jfluchem.2009.11.001
• 作为产物：
  描述：

  氟烷 在 sodium dithionite 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以73.3%的产率得到sodium 1-chloro-2,2,2-trifluoroethanesulfinate
  参考文献：
  名称：

  An easy preparation of per- and poly-fluoroalkyl propenyl sulfones

  摘要：

  Sodium tridecafluorohexanesulfinate (1a) and sodium 1-chloro-2,2,2-trifluoroethanesulfinate (1b) were prepared by the treatment of 1-iodo-tridecafluorohexane and 1-bromo-1-chloro-2,2,2-trifluoroethane with sodium dithionite in a water-acetonitrile solution. Prolonged reaction of 1a with allyl bromide in DMF afforded tridecafluorohexane 1-propenyl sulfone 2 as the only product in good yield. A similar treatment of 1b gave exclusively 1-chloro-2,2,2-trifluoroethane 3-propenylsulfone 4. Bromination of 4 followed by dehydrobromination with Et3N resulted in a mixture of 1-chloro-2,2,2-trifluoroethane 3-bromo-1-propenyl sulfone 6 and 1-chloro-2,2,2-trifluoroethane 2-bromo-3-propenyl sulfone 7, while dehydrobromination with pyridine gave sulfone 6 practically as the only product. alpha,beta-Unsaturated sulfones 2 and 6 were shown to be active dienophiles. (C) 2005 Elsevier B.V All lights reserved.

  DOI：

  10.1016/j.jfluchem.2005.02.014

文献信息

• Insight into “entrainment” in SRN1 reactions of 2,2-dichloro-1,1,1-trifluoroethane(HCFC-123) with thiolates initiated by Na2S2O4
  作者：Xiao-Jun Tang、Qing-Yun Chen

  DOI：10.1016/j.jfluchem.2014.10.006

  日期：2015.1

  An interesting entrainment process in S(RN)1 reactions of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123) with thiolates were studied by experiments and DFT calculations. The radical-anion intermediate, generated from coupling of the fluorinated radical with the thiolate was considered as the key intermediate in this reaction. (C) 2014 Elsevier B.V. All rights reserved.
• HUANG, WEI-YUAN;CHEN, JIAN-LONG, ACTA CHIM. SIN., 45,(1987) N 5, 445-449
  作者：HUANG, WEI-YUAN、CHEN, JIAN-LONG

  DOI：——

  日期：——
• An easy preparation of per- and poly-fluoroalkyl propenyl sulfones
  作者：Wojciech Dmowski、Krystyna Piasecka-Maciejewska

  DOI：10.1016/j.jfluchem.2005.02.014

  日期：2005.6

  Sodium tridecafluorohexanesulfinate (1a) and sodium 1-chloro-2,2,2-trifluoroethanesulfinate (1b) were prepared by the treatment of 1-iodo-tridecafluorohexane and 1-bromo-1-chloro-2,2,2-trifluoroethane with sodium dithionite in a water-acetonitrile solution. Prolonged reaction of 1a with allyl bromide in DMF afforded tridecafluorohexane 1-propenyl sulfone 2 as the only product in good yield. A similar treatment of 1b gave exclusively 1-chloro-2,2,2-trifluoroethane 3-propenylsulfone 4. Bromination of 4 followed by dehydrobromination with Et3N resulted in a mixture of 1-chloro-2,2,2-trifluoroethane 3-bromo-1-propenyl sulfone 6 and 1-chloro-2,2,2-trifluoroethane 2-bromo-3-propenyl sulfone 7, while dehydrobromination with pyridine gave sulfone 6 practically as the only product. alpha,beta-Unsaturated sulfones 2 and 6 were shown to be active dienophiles. (C) 2005 Elsevier B.V All lights reserved.
• Halogen migration vs. hydrogen halogenide elimination in reactions of 1-chloro-2,2,2-trifluoroethansulfonyl chloride and 1,2,2,2-tetrafluoroethansulfonyl fluoride with amines: theoretical and experimental investigation
  作者：Yuriy M. Pustovit、Anatoliy N. Alekseenko、Nikolai D. Volkov、Mykhailo Yu. Fedorchuk、Alexander B. Rozhenko

  DOI：10.1016/j.jfluchem.2009.11.001

  日期：2010.2

  2,2-trifluoroethansulfonylchloride the chlorine migration proceeds forming the corresponding salts of 1,1-dichloro-2,2,2-trifluoroethansulfinic acid. This process as well as the alternative reaction, elimination of hydrogen halogenide, has been studied using quantum chemistry (DFT and MP2) methods. As the calculation data indicate, an intermediately formed anion undergo intramolecular chlorine migration

  已经提出了一种简单且有用的方法来制备1-氯-2,2,2-三氟乙磺酸磺酰氯。通过1-氯-2，2，2-三氟乙磺酰氯的氨解，氯迁移进行，形成1，1-二氯-2，2，2-三氟乙亚磺酸的相应盐。已经使用量子化学（DFT和MP2）方法研究了该过程以及替代反应，即消除卤化氢。如计算数据所示，中间形成的阴离子经由三元环状过渡态经历分子内氯迁移。后者的特征在于低的活化能（ΔE  ＝ 27.0kcal / mol）。在1,2,2,2-四氟乙硫磺酰氟的情况下，活化的障碍要高得多（ΔE ＝ 41.6kcal / mol）。1,1-二氯-2,2,2-三氟乙磺酸亚磺酸和1,1,2,2,2-五氟乙亚磺酸阴离子的结构可以认为是全卤代烷基阴离子与SO 2的供体-受体配合物。