N,N'-Di-tert-butyl-N,N'-dinitroso-1,2-diamino-aethan | 67741-55-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-Di-tert-butyl-N,N'-dinitroso-1,2-diamino-aethan
• 英文别名: N-tert-butyl-N-[2-[tert-butyl(nitroso)amino]ethyl]nitrous amide
• CAS: 67741-55-3
• 化学式: C₁₀H₂₂N₄O₂
• 分子量: 230.31
• InChiKey: LIKPJFFUWHDAAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  65.34
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N,N'-Di-tert-butyl-N,N'-dinitroso-1,2-diamino-aethan 生成 erythro-2,2'-Bipiperidin
  参考文献：
  名称：

  SEEBACH D.; DACH R.; ENDERS D.; RENGER B.; JANSEN M.; BRACHTEL G., HELV. CHIM. ACTA, 1978, 61, NO 5, 1628-1647

  摘要：

  DOI：
• 作为产物：
  描述：

  N-叔-丁基-N-甲基亚硝酰胺 生成 N,N'-Di-tert-butyl-N,N'-dinitroso-1,2-diamino-aethan
  参考文献：
  名称：

  1, 4, 5, 6-Tetrahydro-?-tetrazin-Derivate

  摘要：

  1, 4, 5, 6‐Tetrahydro‐ν‐tetrazin‐DerivateThe title compounds 2 and 13 are readily available from α‐lithiated N‐alkyl‐nitrosoamines 1 (see Tables 1 and 2) which decompose at − 73° to yield the N‐oxides 2. The ESR. spectra of two derivatives 1 are recorded (Fig. 1), and tentative mechanisms are proposed for the head to head dimerizations (la‐ 3‐ 4‐ 5‐ 2a and Scheme 1). Coupling of lithionitrosoamines with iodine (‐6) and alternative decomposition routes of representatives of this class of organometallics with special substitution [equations (2)‐(5)] are reported.The structures of the tetrazines are established by spectroscopic data [ESCA] (Fig. 2), IR., UV., 1H‐ (cf. Fig. 9) and 13C‐NMR., PE. (Scheme 2), by an X‐ray analysis of 2a (Fig. 4‐8 and Table 3), and by the chemical reactions. The crystal structure of 2a is a twisted boat with non planar terminal nitrogen atoms which reflects the electron repulsion in the 4‐atom‐6‐electron NNNN‐system. Comparisons are made with 2‐tetrazenes, the open chain analogues of 13, wherever possible. Raney‐Ni reductions of 2 or 13 gives diamines 14 to which is assigned the d, l‐configuration through the 1H‐NMR. spectra of the aminals 7 and 15. Neither the oxides 2 nor the tetrazines 13 undergo cycloaddition reactions [equation (6) and Section 4].Compound 2a is dimerized to the bis (nitrosoamino)‐2‐tetrazene 18 by treatment with acid, ZnII, CuI or iodomethane. 2a is oxidized at nitrogen to the ethylene diamine derivative 6a (through 20, with H2O2), or at the CH2‐groups of the ring to give oxo‐N‐oxide 21 (with MnO2 or the ring contracted oxo‐tetrazoline‐N‐oxide 22 (with KMnO4).Pyrolysis or photolysis of the dimethyl tetrahydrotetrazine 13a furnishes the trimer 26 of N‐methylimine, but no diazetidine 27. Silver and mercury complexes 29 are obtained from 13a, while Cr(CO)5. THF does not furnish a complex as with azocompounds, but rather replaces N2 in 13a by CO (→ 28). Oxidation with permanganate converts 13a into the oxalic acid derivative 30 with unchanged tetrazine structure.

  DOI：

  10.1002/hlca.19780610512