(E)-1-tert-butyl-4-methyl-5-(methylamino)-4,5-dihydro-1H-tetrazole | 1026091-45-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-1-tert-butyl-4-methyl-5-(methylamino)-4,5-dihydro-1H-tetrazole
• CAS: 1026091-45-1
• 化学式: C₇H₁₅N₅
• 分子量: 169.23
• InChiKey: JTORFFGEXRAPET-SOFGYWHQSA-N

反应信息

• 作为反应物：
  描述：

  (E)-1-tert-butyl-4-methyl-5-(methylamino)-4,5-dihydro-1H-tetrazole 以 氘代四氢呋喃 为溶剂， 以50%的产率得到(etrt-butyl)(1,2-dimethyldiaziridin-3-ylidene)amine
  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