p-chlorophenyl-t-butyl-diazene | 80228-01-9

• 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: p-chlorophenyl-t-butyl-diazene
• 英文别名: 1-(tert-butyl)-2-(4-chlorophenyl)-diazene；Tert-butyl-(4-chlorophenyl)diazene
• CAS: 80228-01-9
• 化学式: C₁₀H₁₃ClN₂
• 分子量: 196.68
• InChiKey: IFXJKYFKRDHQRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  p-chlorophenyl-t-butyl-diazene 在 过氧化氢苯甲酰 作用下， 以 氯仿 为溶剂， 反应 16.0h， 生成 N-tert-Butyl-N'-(4-chloro-phenyl)-diazene N-oxide
  参考文献：
  名称：

  Synthesis of 1-tert-butyl-2-aryldiazene-2-oxides by reactions of t-BuNHMgBr with nitrobenzenes

  摘要：

  A new method has been developed for the synthesis of alkylaryldiazene oxides by the reactions of t-BuNHMgBr with nitrobenzenes. The cis-azoxy compound 1-tert-butyl-2-(2-chlorophenyl)diazene-2-oxide, which irreversibly isomerizes to the trans isomer upon heating, was obtained for the first time under chemical reaction conditions.

  DOI：

  10.1007/bf00961304
• 作为产物：
  描述：

  p-chlorobenzenediazonium tetrafluoroborate 、 碘代叔丁烷 在 双氧水 、 iron(II) sulfate 、 二甲基亚砜 作用下， 以63%的产率得到p-chlorophenyl-t-butyl-diazene
  参考文献：
  名称：

  Polar effects in reactions of carbon-centered radicals with diazonium salts: free-radical diazo coupling

  摘要：

  Carbon-centered radicals react with diazonium salts by addition, leading under reductive conditions to azo derivatives (free-radical diazocoupling), or by electron-transfer in chain processes. The reaction is highly sensitive to polar effects and it has been investigated by three different processes: (i) alkyl radicals, generated from alkyl iodides, H2O2, Fe(II) salt, and DMSO, have been utilized to develop a new general synthesis of alkylarylazo compounds; (ii) the reaction of aryl radicals with diazonium salts in the presence of Ti(III) or Fe(II) salts has been investigated, also in relation to the fact that the reaction products (azoarenes and biaryls) are often detected as side products in classical organic reactions of diazonium salts, catalyzed by Cu(I) salts, such as the Sandmeyer, Meerwein, and Pschorr reactions; (iii) adducts from addition of aryl radicals to vinyl acetate or vinyl ether react with diazonium salts either by diazocoupling reaction or by electron-transfer; a general synthesis of [alpha-(acyl-oxy)alkyl]arylazo compounds has been developed.

  DOI：

  10.1021/jo00040a038

文献信息

• Synthetic Route to Phenyl Diazenes and Pyridazinium Salts from Phenylazosulfonates
  作者：Susanne Gradl、Johannes Köckenberger、Janina Oppl、Martin Schiller、Markus R. Heinrich

  DOI：10.1021/acs.joc.1c00013

  日期：2021.5.7

  synthesis of pyridazinium salts was achieved from readily available phenylazosulfonates in a single reaction step. The reaction proceeds via the formation of short-lived phenyldiazenes, which—owing to the strongly acidic conditions—are partially protonated. The phenyldiazenes then undergo a rapid cycloaddition to furans to give pyridazinium salts via elimination of water. The fact that the pyridazinium synthesis

  吡嗪鎓盐的合成是在一个反应​​步骤中由易于获得的苯基偶氮磺酸盐实现的。该反应通过形成短寿命的苯基二氮烯而进行，该苯基二氮烯由于强酸性条件而部分质子化。然后将苯基二氮烯经历快速环加成反应生成呋喃，从而通过除水得到吡嗪鎓盐。尽管苯基重氮作为中间体存在，但哒嗪鎓合成对氧的敏感性较低，这一事实可以通过非常快速的环加成步骤和苯基二氮杂的部分质子化来解释。
• New general and convenient sources of alkyl radicals, useful for selective syntheses
  作者：Francesca Fontana、Francesco Minisci、Elena Vismara

  DOI：10.1016/s0040-4039(01)91377-2

  日期：1987.1

  Alkyl radicals are obtained from alkyl icdides under very simple conditions and with cheap reagents: i) H2O2 and DMSO; ii) H2O2 and acetone; iii) t-BuOOH. The alkyl radicals can be utilized for selective syntheses, mainly selective formation of carbon-carbon bonds.

  烷基是在非常简单的条件下用廉价的试剂从烷基碘化物获得的：i）H 2 O 2和DMSO；ii）H 2 O 2和丙酮；iii）t-BuOOH。烷基可用于选择性合成，主要是碳-碳键的选择性形成。
• A General Method to Diverse Cinnolines and Cinnolinium Salts
  作者：Dongbing Zhao、Qian Wu、Xiaolei Huang、Feijie Song、Taiyong Lv、Jingsong You

  DOI：10.1002/chem.201300155

  日期：2013.5.10

  Rhodium catalysis: A highly efficient and general method has been established to prepare cinnolines, cinnolinium salts, and polycyclic cinnolinium salts through the rhodium(III)‐catalyzed oxidative CH activation/cyclization of azo compounds with alkynes (see scheme). Key features of this methodology include the unprecedented capacity to create both cinnoline and cinnolinium frameworks.

  铑催化：已经建立了一种高效且通用的方法，通过铑（III）催化的炔烃对偶氮化合物的氧化CH活化/环化反应来制备cinnoline，cinnolinium盐和多环cinnolinium盐（参见方案）。该方法的主要特点包括创建辛诺啉和cinnolinium框架的空前能力。
• Free-radical diazocoupling. A new general reaction of diazonium salts
  作者：Attilio Citterio、Francesco Minisci

  DOI：10.1021/jo00348a033

  日期：1982.4
• Polar effects in reactions of carbon-centered radicals with diazonium salts: free-radical diazo coupling
  作者：Francesco Minisci、Fausta Coppa、Francesca Fontana、Giuseppe Pianese、Lihua Zhao

  DOI：10.1021/jo00040a038

  日期：1992.7

  Carbon-centered radicals react with diazonium salts by addition, leading under reductive conditions to azo derivatives (free-radical diazocoupling), or by electron-transfer in chain processes. The reaction is highly sensitive to polar effects and it has been investigated by three different processes: (i) alkyl radicals, generated from alkyl iodides, H2O2, Fe(II) salt, and DMSO, have been utilized to develop a new general synthesis of alkylarylazo compounds; (ii) the reaction of aryl radicals with diazonium salts in the presence of Ti(III) or Fe(II) salts has been investigated, also in relation to the fact that the reaction products (azoarenes and biaryls) are often detected as side products in classical organic reactions of diazonium salts, catalyzed by Cu(I) salts, such as the Sandmeyer, Meerwein, and Pschorr reactions; (iii) adducts from addition of aryl radicals to vinyl acetate or vinyl ether react with diazonium salts either by diazocoupling reaction or by electron-transfer; a general synthesis of [alpha-(acyl-oxy)alkyl]arylazo compounds has been developed.