(Z)-1-tert-butyl-2-fluoroethene | 6418-03-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (Z)-1-tert-butyl-2-fluoroethene
• 英文别名: (Z)-1-fluoro-3,3-dimethylbut-1-ene
• CAS: 6418-03-7
• 化学式: C₆H₁₁F
• 分子量: 102.152
• InChiKey: MKFGAUYSRZJAGF-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-3,3-dimethyl-1-butenyl(phenyl)iodonium tetrafluoroborate 以 氯仿 为溶剂， 反应 40.0h， 以78%的产率得到3,3-二甲基-1-丁炔
  参考文献：
  名称：

  Thermal decomposition of alkenyliodonium tetrafluoroborates: a novel route to fluoroalkenes

  摘要：

  Alkenyl(phenyl)iodonium tetrafluoroborates dissolved in chloroform, or in the solid state, decompose thermally at 60 degrees C to yield fluoroalkenes and iodobenzene as major products via an S(N)1- or S(N)2-type reaction within the ion pair of the substrates. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00788-7

文献信息

• Kinetics of alkylhalocarbene rearrangements: modulation by fluorine substituents
  作者：Robert A. Moss、Guo Jie Ho、Weiguo Liu

  DOI：10.1021/ja00029a025

  日期：1992.1

  Rate constants were measured by laser flash photolytic methods for hydrogen and carbon 1,2-migrations in four different alkylchlorocarbenes and in the analogous alkylfluorocarbenes. The carbenes, products, and rate constants (s-1) were as follows: phenoxymethylchlorocarbene to (Z)- and (E)-1-chloro-2-phenoxyethene (Z/E approximately 4/1), k = 3.6 x 10(7); phenoxymethylfluorocarbene to (Z)-1-fluoro-2-phenoxyethene (Z/E > 10/1), k = 1.3 x 10(7); neopentylchlorocarbene to (Z)- and (E)-1-tert-butyl-2-chloroethene (Z/E = 1/12), k = 1.4 x 10(7); neopentylfluorocarbene to (Z)- and (E)-1-tert-butyl-2-fluoroethene (Z/E = 1/2.5), k = 2.6 X 10(6); cyclobutylchlorocarbene to 1-chlorocyclopentene (C migration) and chloromethylenecyclobutane (H migration), k(c) = 4.6 X 10(7), k(H) = 2.1 X 10(7); cyclobutylfluorocarbene to 1-fluorocyclopentene (C migration) and fluoromethylenecyclobutane (H migration), k(c) = 1.8 x 10(6), k(H) = 5.3 x 10(5); cyclopropylchlorocarbene to 1-chlorocyclobutene, k = 9 x 10(5); cyclopropylfluorocarbene to 1-fluorocyclobutene, k = 1.4 x 10(5). Activation energies for several of these processes were in the range of 2-4 kcal/mol, with A approximately 10(8)-10(9) s-1.