| 1266110-85-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1266110-85-3
• 化学式: C₁₀H₃F₁₉OS
• 分子量: 532.169
• InChiKey: DNSIABVNUZPXGT-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  全氟己基碘烷 、 以60%的产率得到
  参考文献：
  名称：

  Synthesis of trifluoromethylated heterocycles using partially fluorinated epoxides

  摘要：

  Reaction of 2-trifluoromethyl- (1) and 2,2-bis(trifluoromethyl)- (2) oxiranes with a variety of sulfur nucleophiles proceeds rapidly and under mild conditions. For example, epoxide 2 reacts with aqueous solution of Na(2)S, producing S[CH(2)C(CF(3))(2)OH](2). Reaction of 2 with Na(2)S(2)O(3) leads to the formation of the corresponding Bunte salt. Interaction of 2 with NaSCN in water proceeds exothermically and results in high-yield formation of cyclic imine 5. Although this material can be isolated, it has limited stability and undergoes cyclotrimerization at ambient temperature, giving the corresponding 1,3,5-triazine. A number of heterocyclic compounds containing pendant -CH(2)C(CF(3))(2)OH group were prepared by the reaction of the corresponding thio-derivatives, such as pyridine-2-thiole with epoxide 2. It was found that fluoride anion catalyzes the reaction of epoxides 1 and 2 with isothiocyanates carrying electron withdrawing groups at nitrogen. The reaction results in nucleophilic cyclization and formation of the corresponding exocyclic imines containing a 1,3-oxothiolane moiety. Carbon disulfide was also found to be active in this process, reacting with epoxides 1 and 2 at ambient to give the corresponding trifluoromethylated 1,3-oxathiolane-2-thiones in 58-65% yield. (c) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2010.11.003