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

Reid Tingley, Keith Vaughan

Research output: Contribution to journalArticleResearchpeer-review

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 languageEnglish
Pages (from-to)1434-1441
Number of pages8
JournalCanadian Journal of Chemistry
Volume84
Issue number10
DOIs
Publication statusPublished - 1 Oct 2006
Externally publishedYes

Keywords

  • Bistriazene
  • Diazepane
  • Diazonium salt
  • Formaldehyde
  • Nuclear magnetic resonance
  • Triazene

Cite this

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title = "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",
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.",
keywords = "Bistriazene, Diazepane, Diazonium salt, Formaldehyde, Nuclear magnetic resonance, Triazene",
author = "Reid Tingley and Keith Vaughan",
year = "2006",
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language = "English",
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pages = "1434--1441",
journal = "Canadian Journal of Chemistry",
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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.

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