phenyl nitrile ylide | 104196-67-0

• 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: phenyl nitrile ylide
• 英文别名: benzonitrile methylide；methylidene(phenylmethylidene)azanium
• CAS: 104196-67-0
• 化学式: C₈H₇N
• 分子量: 117.15
• InChiKey: KOTCOFTWCTUDTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  phenyl nitrile ylide 在 水 作用下， 以 乙腈 为溶剂， 生成 Phenyl-2-azaallenium-ion
  参考文献：
  名称：

  [3 + 2] Cycloadditions and Protonation by Alcohols of Photochemically Generated Nitrile Ylides from 2H-Azirines. Formation and Reactivities of Azaallenium Cations

  摘要：

  On photolysis of 2H-phenylazirines id acetonitrile or alcohol solution with 248 nm laser light, phenylnitrile ylides are formed by heterolytic cleavage of the C-C bond of the azirines. The absorption spectra of the ylides are characterized by two strong bands, at ca. 240 and 280 nm, and a weak band, at 380 nm. Electron-deficient olefins react with the nitrile ylides by 1,3-dipolar cycloaddition to yield 5-membered N-heterocycles (rate constants between 4 x 10(5) and 7 x 10(9) M-1 s(-1), the Hammett-p value for the para-substituent on the phenyl ring is -0.9). In alcohols as solvents, the nitrile ylides are protonated to yield azaallenium cations, whose spectroscopic properties and reactivities with nucleophiles are described. The protonation rates of the ylides in alcohols increase with the acidity of the alcohol. On the basis of the large kinetic isotope effect for protonation of ylide by alcohol (k(H)/k(D) = 5.5), the transition state for the ylide protonation is concluded to be linear.

  DOI：

  10.1021/ja971648n
• 作为产物：
  描述：

  3-phenyl-2H-azirine 以 not given 为溶剂， 反应 2.5h， 生成 phenyl nitrile ylide
  参考文献：
  名称：

  氮基中3-苯基-2H-叠氮基腈基腈的分子结构

  摘要：

  DOI：

  10.1021/j100281a018

文献信息

• Carbene and silicon routes as methods for the generation and dipolar cycloaddition reactions of methyl nitrile ylide
  作者：Albert. Padwa、John R. Gasdaska、Miguel. Tomas、Nicholas J. Turro、Yuan. Cha、Ian R. Gould

  DOI：10.1021/ja00281a046

  日期：1986.10
• Heimgartner, Heinz, Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 58, # 1-4, p. 281 - 293
  作者：Heimgartner, Heinz

  DOI：——

  日期：——
• HEIMGARTNER, HEINZ, PHOSPH., SULFUR AND SILICON AND RELAT. ELEM., 58-59,(1991) N-4, C. 281-29+
  作者：HEIMGARTNER, HEINZ

  DOI：——

  日期：——