Abstract
A new series of bistriazenes, the 1-aryl-2-[3-(3-[2-aryl-1-diazenyl]-1,3- diazepan-1-ylmethyl)-1,3-diazepan-1-yl]-1-diazenes (8), has been synthesized from the reaction of diazonium salts with a mixture of 1,4-diaminobutane and formaldehyde. All new compounds of series 8 have been characterized by IR and NMR spectroscopy, and the elemental composition of selected examples has been verified by elemental analysis. The connectivity of the series has been unequivocally determined by X-ray crystallography. The new bistriazenes are important because the structure contains the novel saturated heterocycle, 1,3-diazepane. The general conclusion of this study is that alkanediamines with three or four carbon atoms in the spacer link between the nitrogen atoms give rise to the linear bicyclic molecules of type 2, in contrast to the case of ethylenediamine (two carbon atoms in spacer link), which affords molecules of type 3, which exemplify the cage structure of type 1.
| Original language | English |
|---|---|
| Pages (from-to) | 1434-1441 |
| Number of pages | 8 |
| Journal | Canadian Journal of Chemistry |
| Volume | 84 |
| Issue number | 10 |
| DOIs | |
| Publication status | Published - 1 Oct 2006 |
| Externally published | Yes |
Keywords
- Bistriazene
- Diazepane
- Diazonium salt
- Formaldehyde
- Nuclear magnetic resonance
- Triazene
Cite this
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Triazene derivatives of (1,x)-diazacycloalkanes. Part VII. Synthesis of a series of 1-aryl-2-[3-(3-[2-aryl-1-diazenyl]-1,3-diazepan-1-ylmethyl)-1,3- diazepan-1-yl]-1-diazenes from the reaction of diazonium salts with mixtures of formaldehyde and 1,4-diaminobutane. / Tingley, Reid; Vaughan, Keith.
In: Canadian Journal of Chemistry, Vol. 84, No. 10, 01.10.2006, p. 1434-1441.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - Triazene derivatives of (1,x)-diazacycloalkanes. Part VII. Synthesis of a series of 1-aryl-2-[3-(3-[2-aryl-1-diazenyl]-1,3-diazepan-1-ylmethyl)-1,3- diazepan-1-yl]-1-diazenes from the reaction of diazonium salts with mixtures of formaldehyde and 1,4-diaminobutane
AU - Tingley, Reid
AU - Vaughan, Keith
PY - 2006/10/1
Y1 - 2006/10/1
N2 - A new series of bistriazenes, the 1-aryl-2-[3-(3-[2-aryl-1-diazenyl]-1,3- diazepan-1-ylmethyl)-1,3-diazepan-1-yl]-1-diazenes (8), has been synthesized from the reaction of diazonium salts with a mixture of 1,4-diaminobutane and formaldehyde. All new compounds of series 8 have been characterized by IR and NMR spectroscopy, and the elemental composition of selected examples has been verified by elemental analysis. The connectivity of the series has been unequivocally determined by X-ray crystallography. The new bistriazenes are important because the structure contains the novel saturated heterocycle, 1,3-diazepane. The general conclusion of this study is that alkanediamines with three or four carbon atoms in the spacer link between the nitrogen atoms give rise to the linear bicyclic molecules of type 2, in contrast to the case of ethylenediamine (two carbon atoms in spacer link), which affords molecules of type 3, which exemplify the cage structure of type 1.
AB - A new series of bistriazenes, the 1-aryl-2-[3-(3-[2-aryl-1-diazenyl]-1,3- diazepan-1-ylmethyl)-1,3-diazepan-1-yl]-1-diazenes (8), has been synthesized from the reaction of diazonium salts with a mixture of 1,4-diaminobutane and formaldehyde. All new compounds of series 8 have been characterized by IR and NMR spectroscopy, and the elemental composition of selected examples has been verified by elemental analysis. The connectivity of the series has been unequivocally determined by X-ray crystallography. The new bistriazenes are important because the structure contains the novel saturated heterocycle, 1,3-diazepane. The general conclusion of this study is that alkanediamines with three or four carbon atoms in the spacer link between the nitrogen atoms give rise to the linear bicyclic molecules of type 2, in contrast to the case of ethylenediamine (two carbon atoms in spacer link), which affords molecules of type 3, which exemplify the cage structure of type 1.
KW - Bistriazene
KW - Diazepane
KW - Diazonium salt
KW - Formaldehyde
KW - Nuclear magnetic resonance
KW - Triazene
UR - http://www.scopus.com/inward/record.url?scp=33847673111&partnerID=8YFLogxK
U2 - 10.1139/V06-123
DO - 10.1139/V06-123
M3 - Article
AN - SCOPUS:33847673111
VL - 84
SP - 1434
EP - 1441
JO - Canadian Journal of Chemistry
JF - Canadian Journal of Chemistry
SN - 0008-4042
IS - 10
ER -