4-Ethylidyneazaniumylphenolate | 144084-91-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Ethylidyneazaniumylphenolate
• CAS: 144084-91-3
• 化学式: C₈H₇NO
• 分子量: 133.15
• InChiKey: BDJUZYYPTMFHPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  27.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  乙腈 、 4-二氮醌 以 1,1,2-三氯三氟乙烷（CFC-113） 为溶剂， 生成 4-Ethylidyneazaniumylphenolate
  参考文献：
  名称：

  Laser flash photolysis studies on 4-oxocyclohexa-2,5-dienylidenes

  摘要：

  Reactions of 4-oxocyclohexa-2,5-dienylidene (1) and two derivatives have been investigated using laser flash photolysis techniques. Photolysis of 4-diazocyclohexa-2,5-dien-1-one (4) in 1,1,2-trichlorotrifluoroethane allows the indirect detection of the corresponding carbene 1. This carbene reacts with triplet oxygen at close to the diffusion-controlled rate, forming the carbonyl 0-oxide (lambda(max) = 470 nm). Reaction of triplet 1 with moderate concentrations of cyclohexane leads to formation of phenoxyl radical (lambda(max) = 395 nm). At high concentrations or in neat cyclohexane the predominant path appears to be carbene insertion into the C-H bond. Other reactions examined include 0-H insertion in methanol and the indirect formation of ylides from acetone, acetonitrile, and pyridine. The reactivity pattern that emerges indicates that carbene 1 and its derivatives, 2 and 3, have triplet ground states and that the singlet-triplet energy gap is moderately large. Ylide formation is only observed when the reactants are present in low concentrations and involve a two-step reaction from the triplet carbene; no ylides are observed in neat acetone or acetonitrile suggesting that for the singlet carbene insertion into C-H bonds is favored over direct ylide formation.

  DOI：

  10.1021/jo00050a020

文献信息

• Laser flash photolysis studies on 4-oxocyclohexa-2,5-dienylidenes
  作者：B. R. Arnold、J. C. Scaiano、G. F. Bucher、W. W. Sander

  DOI：10.1021/jo00050a020

  日期：1992.11

  Reactions of 4-oxocyclohexa-2,5-dienylidene (1) and two derivatives have been investigated using laser flash photolysis techniques. Photolysis of 4-diazocyclohexa-2,5-dien-1-one (4) in 1,1,2-trichlorotrifluoroethane allows the indirect detection of the corresponding carbene 1. This carbene reacts with triplet oxygen at close to the diffusion-controlled rate, forming the carbonyl 0-oxide (lambda(max) = 470 nm). Reaction of triplet 1 with moderate concentrations of cyclohexane leads to formation of phenoxyl radical (lambda(max) = 395 nm). At high concentrations or in neat cyclohexane the predominant path appears to be carbene insertion into the C-H bond. Other reactions examined include 0-H insertion in methanol and the indirect formation of ylides from acetone, acetonitrile, and pyridine. The reactivity pattern that emerges indicates that carbene 1 and its derivatives, 2 and 3, have triplet ground states and that the singlet-triplet energy gap is moderately large. Ylide formation is only observed when the reactants are present in low concentrations and involve a two-step reaction from the triplet carbene; no ylides are observed in neat acetone or acetonitrile suggesting that for the singlet carbene insertion into C-H bonds is favored over direct ylide formation.