1-tert-butyl-5-(methylamino)tetrazolium tetrafluoroborate | 1026091-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-tert-butyl-5-(methylamino)tetrazolium tetrafluoroborate
• 英文别名: 1-tert-butyl-N-methyl-2H-tetrazol-1-ium-5-amine;tetrafluoroborate
• CAS: 1026091-84-8
• 化学式: BF₄*C₆H₁₃N₅*H
• 分子量: 243.015
• InChiKey: XDIFCKUUROVQSS-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 1-tert-butyl-5-(methylamino)tetrazolium tetrafluoroborate 以 乙醚 、 乙腈 为溶剂， 生成 、 1-tert-butyl-4-methyl-5-(N-methylamino)tetrazolium tetrafluoroborate
  参考文献：
  名称：

  Iminodiaziridines by Regio- and Stereoselective Cyclization of Diastereomeric Singlet Triazatrimethylenemethane Diradicals Generated Through Photolysis of 5-Imino-4,5-dihydro-1H-tetrazoles

  摘要：

  1,4-Dialkyl-5-(N-alkylimino)-4,5-dihydro-1H-tetrazoles were prepared in high yields by deprotonation with sodium hydride of 1,4-dialkyl-5-(N-alkylamino)tetrazolium salts that were adorned with two or three different alkyl groups, including methyl, trideuteriomethyl, and tert-butyl groups. Direct irradiation (lambda > 255 nm) at -60 degrees C yielded molecular nitrogen and mixtures of 1,2-dialkyl-3-(N-alkylimino)diaziridines (83-87%) along with carbodiimides (13-17%) arising by 1,3-dipolar cycloreversion. The missing 1,3-dipoles, alkyl azides, did not survive photolysis. Each member of a pair of isotopomers and of a pair of isomers, and an iminodihydrotetrazole, whose three nitrogens were tagged, yielded a characteristic mixture of three isomeric iminodiaziridines that allowed the mode of formation to be deduced. The results are interpreted in terms of photodenitrogenation of the iminodihydrotetrazoles to furnish diastereomeric singlet triazatrimethylenemethane diradicals that retain the inherited configurations before ring closure to iminodiaziridines, presumably in two steps via mono-orthogonal diradicals.

  DOI：

  10.1021/jo702697f
• 作为产物：
  描述：

  N-tert-butyl-N'-methylcarbodiimide 在 sodium azide 、 氯化铵 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 1-tert-butyl-5-(methylamino)tetrazolium tetrafluoroborate
  参考文献：
  名称：

  Iminodiaziridines by Regio- and Stereoselective Cyclization of Diastereomeric Singlet Triazatrimethylenemethane Diradicals Generated Through Photolysis of 5-Imino-4,5-dihydro-1H-tetrazoles

  摘要：

  1,4-Dialkyl-5-(N-alkylimino)-4,5-dihydro-1H-tetrazoles were prepared in high yields by deprotonation with sodium hydride of 1,4-dialkyl-5-(N-alkylamino)tetrazolium salts that were adorned with two or three different alkyl groups, including methyl, trideuteriomethyl, and tert-butyl groups. Direct irradiation (lambda > 255 nm) at -60 degrees C yielded molecular nitrogen and mixtures of 1,2-dialkyl-3-(N-alkylimino)diaziridines (83-87%) along with carbodiimides (13-17%) arising by 1,3-dipolar cycloreversion. The missing 1,3-dipoles, alkyl azides, did not survive photolysis. Each member of a pair of isotopomers and of a pair of isomers, and an iminodihydrotetrazole, whose three nitrogens were tagged, yielded a characteristic mixture of three isomeric iminodiaziridines that allowed the mode of formation to be deduced. The results are interpreted in terms of photodenitrogenation of the iminodihydrotetrazoles to furnish diastereomeric singlet triazatrimethylenemethane diradicals that retain the inherited configurations before ring closure to iminodiaziridines, presumably in two steps via mono-orthogonal diradicals.

  DOI：

  10.1021/jo702697f