1-tert-Butyl-2-phenyldiazen | 1775-83-3

• 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: 1-tert-Butyl-2-phenyldiazen
• 英文别名: 2-Methyl-2-phenylazo-propan；Diazene, tert-butyl-phenyl；tert-butyl(phenyl)diazene
• CAS: 1775-83-3
• 化学式: C₁₀H₁₄N₂
• 分子量: 162.235
• InChiKey: LDIGAIASAKXTON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 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：

  1-tert-Butyl-2-phenyldiazen 在 铂 氢气 作用下， 以 乙醇 为溶剂， 生成 N-tert.Butyl-N'-phenylhydrazin
  参考文献：
  名称：

  Structures of the 1:1:1 adducts of the nitroso-isonitrile-isocyanate reaction. Possible intermediacy of a carbodiimide N-oxide

  摘要：

  DOI：

  10.1021/jo00909a021
• 作为产物：
  描述：

  N-(tert.-Butyl)-N'-phenyldiazen-N'-oxid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 1-tert-Butyl-2-phenyldiazen
  参考文献：
  名称：

  Novel, directed synthesis of unsymmetrical azoxyalkanes and azoxyaralkanes from N,N-dihaloamine and nitroso precursors

  摘要：

  DOI：

  10.1021/jo00934a006

文献信息

• Electron transfer free radical mechanism in the reactions of arenediazonium cations with grignard reagents
  作者：P.R. Singh、R.K. Khanna、B. Jayaraman

  DOI：10.1016/0040-4039(82)80161-5

  日期：1982.1

  The major pathway in the reactions of arenediazonium cations with certain Grignard reagents is found to involve an electron transfer from the latter to the π-system of the former reactant and radicals are the immediate precursors of the final products.

  人们发现，苯二氮杂阳离子与某些格氏试剂反应的主要途径涉及电子从后者转移至前反应物的π系统，自由基是最终产物的直接前体。
• Radical Switch Reaction. A Novel Reaction between Two Free Radicals in a Solvent Cage
  作者：Michio Kobayashi、Michiko Gotoh、Masato Yoshida

  DOI：10.1246/bcsj.60.295

  日期：1987.1

  Studies on the thermal decomposition of t-butyl phenylazo sulfone suggested the occurrence of a radical switch reaction, a novel type of reaction between two radicals. A primary geminate radical pair, t-butanesulfonyl and phenyl radical pair, exchange sulfur dioxide to form a new radical pair consisting of t-butyl and benzenesulfonyl radicals. The generation of benzenesulfonyl radical was confirmed

  对叔丁基苯基偶氮砜热分解的研究表明发生了自由基转换反应，这是两种自由基之间的一种新型反应。主要的成对自由基对，叔丁烷磺酰基和苯基自由基对，交换二氧化硫以形成由叔丁基和苯磺酰基自由基组成的新自由基对。苯磺酰基自由基的产生通过其ESR光谱和含有苯磺酰基的产物的分离得到证实。
• 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。
• Garst, Michael E.; Lukton, David, Synthetic Communications, 1980, vol. 10, # 2, p. 155 - 160
  作者：Garst, Michael E.、Lukton, David

  DOI：——

  日期：——
• 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.