thiazolium triflate | 155521-36-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: thiazolium triflate
• 英文别名: Thiazole triflate；1,3-thiazole;trifluoromethanesulfonic acid
• CAS: 155521-36-1
• 化学式: CHF₃O₃S*C₃H₃NS
• 分子量: 235.208
• InChiKey: JTYVBPJUVNSXEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [1,1'-bis(diphenylphosphino)ferrocene](η(2)-ethene)platinum 、 thiazolium triflate 以 甲醇 、 二氯甲烷 为溶剂， 生成 、
  参考文献：
  名称：

  Scope of the C-S Insertion Reaction of Thiazolium Salts with Platinum(0) Diphosphine Complexes

  摘要：

  When 3-methylthiazolium iodide or BF4- is reacted with 1,1'-bis(diphenylphosphino)ferrocene-eta(2)-ethene- platinum (10) above 40 degrees C, a rapid displacement reaction occurs, leading to the formation of a ring-expanded adduct 11 by formal C-S insertion; a 2:1 adduct 12 is formed sequentially. Thiazole, its N-oxide, and oxazole do not show this type of reactivity under these conditions, although a related 1:1 adduct is formed by thiazole HO3SCF3, and both 1:1 and 2:1 adducts from the benzothiazole BF3 complex. With 2,3-dimethylthiazolium BF4-, the reaction is much slower and the product 14 arises from a C-S insertion reaction of opposite regiochemistry. With 3-methylbenzothiazolium BF4-, a similar sequence occurs, and the 1:1 adduct 17 and the 2:1 adduct 18 have been characterized crystallographically. In the benzothiazolium series, the 2,3-dimethyl derivative behaves similarly to the parent, giving product 19. Similar chemistry was observed initially with 2-chloro-3-methylbenzothiazolium BF4- on reaction with 10, but rearrangement occurs subsequently to give the C-Cl insertion product 21. C-S cleavage of S,N,N-trimethylthioformamidinium BF4- is observed on reaction with 10, giving the C-S insertion product 22. Electrospray MS played an important role in determining the solution structures of several of the Pt complexes described.

  DOI：

  10.1021/ja00091a023