hexamethylguanidinium-azide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: hexamethylguanidinium-azide
• 英文别名: Hexamethyl-guanidinium；Hexamethylguanidinium azide；bis(dimethylamino)methylidene-dimethylazanium;azide
• 化学式: C₇H₁₈N₃*N₃
• 分子量: 186.26
• InChiKey: TYMGXEIHUHLHPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  hexamethylguanidinium-azide 在 溴乙酸乙酯 作用下， 以 二氯甲烷 为溶剂， 生成 1,1,2,2,3,3-Hexamethylguanidiniumbromid
  参考文献：
  名称：

  Synthesis and Azidolysis of 2-Chlorotetramethylguanidine. Synthetic Utility of Hexa- and Tetramethylguanidinium Azide

  摘要：

  DOI：

  10.1021/jo01343a026
• 作为产物：
  描述：

  hexamethylguanidinium methylcarbonate 在 叠氮基三甲基硅烷 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以62%的产率得到hexamethylguanidinium-azide
  参考文献：
  名称：

  Synthesis of Organic (Trimethylsilyl)chalcogenolate Salts Cat[TMS-E] (E = S, Se, Te): the Methylcarbonate Anion as a Desilylating Agent

  摘要：

  A high-yield synthesis of the class of (trimethylsilyl)chalcogenolate organic salts [Cat] [TMS-E] (E = S, Se, Te; Cat = BMPyr, DMPyr, NMe4, nBu(3)MeP) is presented. The title compounds have been prepared by the strictly aprotic reaction between the respective bis- se (trimethylsilyl)chalcogenide (TMS,E) and methylcarbonate ionic liquids (ILs). This constitutes a novel reaction behavior of methylcarbonate ILs, acting as a nudeophilic desilylating agent and a Lewis base instead of as a Bronsted base. Thus prepared silylchalcogenolate salts represent an activated form of the multifunctional TMS2E reactant series. Pyrrolidinium TMS-S salts have proven to be excellent precursors for the synthesis of pyrrolidinium hexasulfides. The scope of the desilylation reaction can be extended to other silyl-bearing synthons such as (trimethylsilyl)azide and (trimethylsilyl)cyanide.

  DOI：

  10.1021/acs.inorgchem.5b01665

文献信息

• Synthesis and Azidolysis of 2-Chlorotetramethylguanidine. Synthetic Utility of Hexa- and Tetramethylguanidinium Azide
  作者：Anthony J. Papa

  DOI：10.1021/jo01343a026

  日期：1966.5
• Synthesis of Organic (Trimethylsilyl)chalcogenolate Salts Cat[TMS-E] (E = S, Se, Te): the Methylcarbonate Anion as a Desilylating Agent
  作者：Lars H. Finger、Benjamin Scheibe、Jörg Sundermeyer

  DOI：10.1021/acs.inorgchem.5b01665

  日期：2015.10.5

  A high-yield synthesis of the class of (trimethylsilyl)chalcogenolate organic salts [Cat] [TMS-E] (E = S, Se, Te; Cat = BMPyr, DMPyr, NMe4, nBu(3)MeP) is presented. The title compounds have been prepared by the strictly aprotic reaction between the respective bis- se (trimethylsilyl)chalcogenide (TMS,E) and methylcarbonate ionic liquids (ILs). This constitutes a novel reaction behavior of methylcarbonate ILs, acting as a nudeophilic desilylating agent and a Lewis base instead of as a Bronsted base. Thus prepared silylchalcogenolate salts represent an activated form of the multifunctional TMS2E reactant series. Pyrrolidinium TMS-S salts have proven to be excellent precursors for the synthesis of pyrrolidinium hexasulfides. The scope of the desilylation reaction can be extended to other silyl-bearing synthons such as (trimethylsilyl)azide and (trimethylsilyl)cyanide.