sek-Cyclopropylethylradikal | 24299-92-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 饱和烃
• 英文名称: sek-Cyclopropylethylradikal
• 英文别名: 1-Cyclopropyl-aethyl
• CAS: 24299-92-1
• 化学式: C₅H₉
• 分子量: 69.1265
• InChiKey: MQCOJUNAOKAPBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  sek-Cyclopropylethylradikal 生成 Pent-2-en-5-yl-Radikal
  参考文献：
  名称：

  Bowry, Vincent W.; Lusztyk, Janusz; Ingold, Journal of the American Chemical Society, 1991, vol. 113, # 15, p. 5687 - 5698

  摘要：

  DOI：
• 作为产物：
  描述：

  以 环己烷 为溶剂， 生成 sek-Cyclopropylethylradikal
  参考文献：
  名称：

  Kinetics of Reactions of Cyclopropylcarbinyl Radicals and Alkoxycarbonyl Radicals Containing Stabilizing Substituents: Implications for Their Use as Radical Clocks

  摘要：

  The rate constants for rearrangement of alpha-substituted cyclopropylcarbinyl radicals have been measured by nitroxide radical-trapping (NPT). Those bearing methyl, dimethyl, or cyclopropyl substituents undergo ring opening 2-3 times more slowly than does cyclopropylmethyl radical, but the reaction is essentially irreversible under the conditions used. Phenyl and tert-butoxycarbonyl alpha-substituents retard the rate of ring opening more strongly and enhance the rate of ring closure of the corresponding substituted but-3-enyl radicals. Thus for c-C(3)H(5)CHPh at 60 degrees C, k(ring open) = 5.4 x 10(5) s(-1), k(ring close) = 1.5 x 10(7) s(-1), and the equilibrium favors the ring closed form (K-equil = 0.04). The implications of the possible reversibility of the ring opening of substituted cyclopropylcarbinyl radicals for cyclopropane probe studies of metal hydride reduction and other chemical/biochemical reactions are assessed. Most of the cyclopropylcarbinyl radicals were generated from tert-butyl peroxyglyoxaletes (ROC(O)CO(3)Bu(t)) via alkoxycarbonyl radicals (ROCO). This method allowed the determination of the rate constants for decarboxylation of ROCO when R is t-Bu, PhCH(2), c-C(3)H(5)CMe(2), c-C(3)H(5)CHMe, (c-C3H5)(2)CH, or c-C3H5CHC6H(5).

  DOI：

  10.1021/ja00086a003