1,3,4,6-Tetramethyl-1,4-dihydro-1,2,4,5-tetrazine, C6H12N4

Hu²

2005

Cryst. Res. Technol.

The title compound, C 22 H 19 N 5 O 2 , was prepared and its structure was determined by X-ray diffraction [CCDC 216074]. The compound crystallizes from ethanol in the orthorhombic system, space group P2 1 2 1 2 1 , with unit cell parameters: a=10.048(1) Å, b= 13.935 (2) Å, c =14.607(2) Å, Z=4, and V=2045.3(5) Å 3. The crystal structure was solved by direct methods and refined by full-matrix least-squares to a final R-value of 0.0516 with 3621 unique reflections. The central six-membered ring of the compound has a boat conformation and is not homoaromatic, in which adjacent atoms N1 and N4 deviate from the plane of the ring by 0.4546(33) Å and 0.3786(33) Å, respectively.

Section: Introductionmentioning

confidence: 99%

Crystal structure of N‐(2‐methoxyphenyl)‐3,6‐diphenyl‐1,4‐dihydro‐1,2,4,5‐tetrazine‐1‐carbonamide

Hu²

2005

Cryst. Res. Technol.

“…16 There still seems to be some doubt as to whether the 1,4-dihydro structures have homoaromaticity. 17,18 In compound 1, the atoms N2, C3, N5 and C6 are coplanar, with the largest deviation from the N2/C3/N5/C6 plane (plane 1) being -0.0321 (13) Å for atom N2. The leastsquares plane is listed in Table 2.…”

mentioning

confidence: 99%

Synthesis and Structure Analysis of N¹,N⁴-di-tert-Butyl-3,6-Dimethyl-1,4-Dihydro-1,2,4,5-Tetrazine-1,4-Dicarboxamide

Journal of Chemical Research

2012

N 1 ,N 4 -Di-tert-butyl-3,6-dimethyl-1,4-dihydro-1,2,4,5-tetrazine-1,4-dicarboxamide was prepared from 3,6-dimethyl-1,6dihydro-1,2,4,5-tetrazine, and its structure was confirmed by single-crystal X-ray diffraction. This reaction yields the 1,4-dicarboxamide derivative rather than the 1,2-dicarboxamide derivative. The central six-member ring of the title compound has a boat conformation and therefore, is not homoaromatic. * Correspondent.

“…For example, X-ray diffraction was reported to show 3,6-bis(4-chlorobenzyl)-1,4-dihydro-1,2,4,5-tetrazine to have an obvious chair conformation without homoaromatic structure, 8 but 1,3,4,6-tetramethyl-1,4dihydro-1,2,4,5-tetrazine was analysed by X-ray diffraction and a possible homoaromatic structure was identified. 9 There seems to be much confusion over the structures of 1,2-and 1,4-dihydro-1,2,4,5-tetrazine isomers, and the same compound is often formulated as both structures. In most cases, the dihydro structure which would be the first reaction product is presented, or the authors have formulated their compounds in the dihydro structure which seemed to be the most accepted at that time.…”

mentioning

confidence: 99%

Synthesis and Structure Analysis of 1-(2-Chlorobenzoyl)-3,6-Diphenyl-1,4-Dihydro-1,2,4,5-Tetrazine

Journal of Chemical Research

Zhang

2012

1-(2-Chlorobenzoyl)-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine was prepared from 2-chlorobenzoyl chloride and 3,6diphenyl-1,2(or 1,4)-dihydro-1,2,4,5-tetrazine, and its structure was determined by X-ray diffraction. This reaction yields the 1,4-dihydro derivative rather than the 1,2-dihydro derivative. The central six-member ring of the title compound exhibits a boat conformation and therefore, is not homoaromatic.