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Author: Grafiati

Published: 10 December 2022

Last updated: 28 January 2023

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1

Iglesias, Bernardo A., Manfredo Hörner, Henrique E. Toma, and Koiti Araki. "5-(1-(4-phenyl)-3-(4-nitrophenyl)triazene)-10,15,20-triphenylporphyrin: a new triazene-porphyrin dye and its spectroelectrochemical properties." Journal of Porphyrins and Phthalocyanines 16, no. 02 (February 2012): 200–209. http://dx.doi.org/10.1142/s1088424612004501.

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The new triazene-porphyrin dye 5-(1-(4-phenyl)-3-(4-nitrophenyl)triazene)-10,15,20-triphenylporphyrin, encompassing a reactive protonated triazene moiety, was prepared starting from meso-tetraphenylporphyrin ( H2TPP ), first converting it to the 5-(4-nitrophenyl)-10,15,20-triphenylporphyrin, then reducing to the 5-(4-aminophenyl)-10,15,20-tri(phenyl)porphyrin intermediate, and reacting with the diazonium salt of 4-nitroaniline; and characterized by spectroscopic and electrochemical methods. The absorption spectrum of the neutral species resembled the sum of H2TPP and of 1,3-bis(4-nitrophenyl)triazene spectrum, but the deprotonated anionic species showed more delocalized frontier orbitals, behaving as a push-pull system exhibiting triazenide-to-porphyrin charge-transfer transitions.

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2

Albertin, Gabriele, Stefano Antoniutti, Marco Bedin, Jesús Castro, and Soledad Garcia-Fontán. "Synthesis and Characterization of Triazenide and Triazene Complexes of Ruthenium and Osmium." Inorganic Chemistry 45, no. 9 (May 2006): 3816–25. http://dx.doi.org/10.1021/ic052063u.

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3

Hartmann, Edmund, Raimund Schmid, and Joachim Strähle. "Synthese von zweikernigen Triazenido- und Pentaazadienidokomplexen des einwertigen Silbers. Kristallstruktur von [Ag(MeOC6H4N3C6H4OM e)]2· 2/3 Py, [Ag(MeOC6H4N5C6H4OMe)]2 und [Ag(EtOC6H4N5C6H4OEt)]2 · Py / Dimeric Triazenido and Pentaazadienido Complexes of Monovalent Silver. Synthesis and Structure of [Ag(MeOC6H4N3C6H4OM e)]2· 2/3 Pyridine, [Ag(MeOC6H4N5C6H4OMe)]2 und [Ag(EtOC6H4N5C6H4OEt)]2 · Pyridine." Zeitschrift für Naturforschung B 44, no. 7 (July 1, 1989): 778–85. http://dx.doi.org/10.1515/znb-1989-0710.

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[Ag(MeOC6H4N3C6H4OMe)]2 (1) is formed in THF from AgNO3 , and the triazenide anion, as obtained from the corresponding triazene and Na. 1 crystallizes from pyridine in the form of orange-yellow , air stable crystals with the com position 1·2/3 C5H5N: space group P 1̅ with a = 1468.0(5), b = 1514.1(6), c - 1316.1(3) pm, a = 113.45(3)°, β = 1 1 4 .8 1 (2 )°, γ = 66.78(3)°, Z - 3. The triazenide ion functions as a bridging ligand forming planar (AgN3)2 heterocycles. The unit cell contains two symmetry-independent dinuclear complexes, one of which is centrosymmetrical. The short Ag -Ag distances of 268.0 and 269.8 pm suggest Ag -Ag bonding. The pentaazadienido complexes Ag(RN5R) with R = p -MeO - C6H4 (2), p -EtO - C6H4 (3), p-Cl -C6H4 (4), p -F -C6H4 (5), are obtained from saturated solutions of the pentaazadiene in conc. NH3 and AgNO3 , as explosive, red precipitates which are stable in air. Crystals of 2 and 3 · C5H5N are obtained from pyridine. 2 crystallizes in the monoclinic space group P21/c: a - 583.7(6), b = 1705.1(9), c = 1489.6(9) pm. β = 96.2(1)°, Z = 2; 3 · C5H5N is triclinic (space group P 1̅) with a = 1160.4(4). b = 1671.0(6), c = 509.0(1) pm. a = 97.51(2)°, β = 97.36(2)°, γ = 81.51(3)°, Z = 1. The complexes 2 and 3 are dinuclear with the pentaazadienide ion as a (N1)-η1,(N5)-η1 bridging ligand in 2 and a (N1)-η1, (N3)-η1 bridging ligand in 3. The bridging mode in 3 results in a short Ag -Ag contact of 283.44 pm. The Ag -N distances range from 210.8 to 215.7 pm in 1 and from 215.0 to 220 pm in (2) and (3).

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4

Hartmann, Edmund, and Joachim Strähle. "Synthese und Struktur von 1,3-Bis(4-trifluormethylphenyl)triazenido-Komplexen des Kupfer(I) und Silber(I) / Synthesis and Structure of 1,3-Bis(4-trifluormethylphenyl)triazenido Complexes of Copper(I) and Silver(I)." Zeitschrift für Naturforschung B 43, no. 7 (July 1, 1988): 818–24. http://dx.doi.org/10.1515/znb-1988-0706.

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[(F3CC6H4NNNC6H4CF3)Cu]4 (1) and [(F3CC6H4NNNC6H4CF3)Ag]n (2) are obtained by the addition of a solution of CuCl or AgNO, in CH3CN to a solution of Na(F3CC6H4NNNC6H4CF3) in THF. Recrystallization of 1 in toluene/n-hexane yields air-stable orange crystals (tetragonal space group P4̄21c, lattice constants a - 1527.7(5), c = 1281.3(4) pm, Z = 2). Complex 1 forms tetrameric units of symmetry S4 with the four Cu atoms forming a slightly folded rhombus. The triazenido ligands bridge the Cu atoms alternatingly above and below the rhombic Cu4 ring resulting in short Cu -Cu interactions of 257.9 pm. Complex 2 crystallizes from pyridine/methanol in form of yellow, air-stable crystals exhibiting a weak temperature independent paramagnetism of 0.64 B.M. per Ag atom at room temperature. The lattice constants are a = 2943(2), b = 475.8(5), c = 2280(1) pm. β = 111.99(6)°. Z = 8 for the monoclinic space group P21/c. The Ag atoms form zigzag chains with short Ag-Ag distances of 283.4 and 284.0 pm and angles Ag-Ag-Ag of 113.7 and 114.1°. The bridging triazenide ligands are arranged alternatingly above and below the Ag-Ag chain. Two symmetry independent zigzag chains are found in the unit cell.

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5

Lee, Wei-Tsung, Matthias Zeller, and Adriana Lugosan. "Bis(triazenide), tris(triazenide), and lantern-type of triazenide iron complexes: Synthesis and structural characterization." Inorganica Chimica Acta 477 (May 2018): 109–13. http://dx.doi.org/10.1016/j.ica.2018.02.014.

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6

McKay, Alasdair I., and Marcus L. Cole. "Structural diversity in a homologous series of donor free alkali metal complexes bearing a sterically demanding triazenide." Dalton Transactions 48, no. 9 (2019): 2948–52. http://dx.doi.org/10.1039/c8dt04983a.

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7

Gyton, Matthew R., Anthony R. Leverett, Marcus L. Cole, and Alasdair I. McKay. "Bulky bis(aryl)triazenides: just aspiring amidinates? A structural and spectroscopic study." Dalton Transactions 49, no. 17 (2020): 5653–61. http://dx.doi.org/10.1039/d0dt00285b.

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8

Shupenyuk, V. I., S. V. Mamykin, T. N. Taras, M. P. Matkivskyi, O. P. Sabadakh, and O. M. Matkivskyi. "Structure and Morphology of Anthraquinone Triazene Films on Silicon Substrate." Фізика і хімія твердого тіла 21, no. 1 (March 29, 2020): 117–23. http://dx.doi.org/10.15330/pcss.21.1.117-123.

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An optimal imposition method of anthraquinone triazenes on silicon lining was selected. This allowed to create a nanometer film that can be used as dielectric aromatic buffer layers. A morphological research of triazene films shows the existence of delocalized globular anthraquinone macromolecular microformation on the background of triazene uneven layers. The oxidized surface of the triazene substrate is applied better than those without the oxide. This is caused by distribution of electron density in triazene which creates an additional Si/SiO2 coupling system and by presence of voluminous aromatic substituents which impairs the uniformity of film deposition and reduces its thickness.

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9

Leverett, Anthony R., Vera Diachenko, Marcus L. Cole, and Alasdair I. McKay. "Kinetic stabilization of low-oxidation state and terminal hydrido main group metal complexes by a sterically demanding N,N′-bis(2,6-terphenyl)triazenide." Dalton Transactions 48, no. 35 (2019): 13197–204. http://dx.doi.org/10.1039/c9dt02562f.

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10

Vaughan, Keith, Elizabeth Turner, and Hilary Jenkins. "1,2-Bis-(1-{3-pyridyl-}3-methyltriazen-3-yl)ethane: Synthesis and X-ray crystal structure." Canadian Journal of Chemistry 82, no. 3 (March 1, 2004): 448–53. http://dx.doi.org/10.1139/v03-213.

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3-Aminopyridine is diazotized in the conventional manner and the diazonium salt coupled with N,N ′-dimethylethylenediamine to afford the title compound (1), which is a potential antitumour agent. The compound has been characterized by spectroscopic methods. The 1H NMR spectrum shows evidence of rotational conformerism, from the observation of broadening of the N-methyl signals in the room-temperature spectrum. Low-temperature NMR spectra (down to 223 K) show the presence of three distinct rotamers. The crystal structure of 1,2-bis-(1-{3-pyridyl-}3-methyltriazen-3-yl)ethane (1) has been determined by single crystal X-ray diffraction analysis. The bis-triazene (1) exists as the "staggered" conformation in the solid state, with an "antianti" configuration around the NN bond of the triazene units. The crystal structure of 1 is compared with the closely related bis-triazene 2 and also compared with the simple mono-triazene 3. Crystal data for 1, C14H18N8: orthorhombic, space group Pbca, a = 11.2550(8) Å, b = 8.8507(6) Å, c = 15.0069(10) Å, β = 90°, and V = 1494.91(18) Å3, for Z = 4.Key words: triazene, bis-triazene, pyridine, X-ray, VT NMR, diazonium coupling.

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11

Hartmann, Edmund, and Joachim Strähle. "Synthese und Kristallstruktur von [l,3-Bis(4-ethoxyphenyl)triazenido]pyridino-silber(I), einem dimeren Komplex mit kurzem Silber-Silber-Kontakt / Synthesis and Crystal Structure of [1,3-Bis(4-ethoxyphenyl)triazenido]pyridino Silver(I), a Dimeric Complex with a Short Silver-Silver Contact." Zeitschrift für Naturforschung B 43, no. 5 (May 1, 1988): 525–28. http://dx.doi.org/10.1515/znb-1988-0506.

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1,3-Bis(4-ethoxyphenyl)triazenido silver(I) (1) is obtained from equimolar amounts of the triazenido anion and AgNO3 in THF/CH3CN. 1 forms in pyridine the dimer [Ag(EtOC6H4NNNC6H4OEt)·py]2 (2) which crystallizes as yellow pyridine solvate 2·2 py in the monoclinic space group P21/n and a = 1067.1(7), b = 1764.5(9), c = 1373.0(9) pm, β = 106.46(7)°, Z = 2. In the centrosymmetric dimer 2, two triazenido ligands bridge two Ag(I) atoms with their atoms N1 and N3 forming an eight-membered heterocycle Ag2N6 with a short Ag-Ag interaction of 272.6 pm. To each Ag atom an additional pyridine ligand is weakly coordinated with a distance Ag-N40 = 245.5 pm. The bond axis N1 - Ag-N3′ within the heterocycle is not linear (158.5°). The Ag-N distances to the N-atoms of the triazenido ligand are 217.6 and 218.5 pm.

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12

Mangawa, Shrawan Kumar, Chiranjeev Sharma, Ashawani kumar Singh, and Satish K. Awasthi. "Expedient and efficient one pot synthesis of trifluoroethyl ethers from metal free 2,4,6-tris-(2,2,2-trifluoro-ethoxy)-[1,3,5] triazene." RSC Advances 5, no. 44 (2015): 35042–45. http://dx.doi.org/10.1039/c5ra00618j.

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13

Kalden, Diana, Sven Krieck, Helmar Görls, and Matthias Westerhausen. "1,3-Bis(2,4,6-trimethylphenyl)triazenides of potassium, magnesium, calcium, and strontium." Dalton Transactions 44, no. 17 (2015): 8089–99. http://dx.doi.org/10.1039/c5dt00595g.

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1,3-Bis(2,4,6-trimethylphenyl)triazenide anions act as bidentate ligands toward s-block metals; in the calcium derivative π-stacking of the aromatic rings leads to additional stabilization of the complex.

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14

Mpofu, Pamburayi, Polla Rouf, Nathan J. O'Brien, Urban Forsberg, and Henrik Pedersen. "Thermal atomic layer deposition of In₂O₃ thin films using a homoleptic indium triazenide precursor and water." Dalton Transactions 51, no. 12 (2022): 4712–19. http://dx.doi.org/10.1039/d1dt03748j.

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In2O3 thin films are deposited using thermal atomic layer deposition with an indium(iii) triazenide precursor and water. The films and deposition process are on par with the previously reported indium(iii) formamidinate.

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15

Doucet, Katherine G., Cory C. Pye, and Thomas G. Enright. "An exploratory ab initio study of the SN2 reaction of 1,3,3-trimethyltriazene with halide ions." Canadian Journal of Chemistry 85, no. 11 (November 1, 2007): 958–63. http://dx.doi.org/10.1139/v07-110.

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Methyltriazene and the O6 oxygen of guanine are believed to undergo a bimolecular nucleophilic substitution (SN2) reaction to form methylguanine, which is proposed to be responsible for the cytotoxic properties of triazene-containing anti-neoplastic agents, such as Dacarbazine. To better understand the proposed mechanism of triazene-containing anti-neoplastic agents, a series of ab initio studies investigating the SN2 reaction between methyltriazenes and halide ions were undertaken. The results of our investigation of the SN2 reaction between 1,3,3-trimethyltriazene and the halide ions are presented here.Key words: triazene, trimethyltriazene, Dacarbazine, Temozolomide, bimolecular nucleophilic substitution reaction.

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16

Li, Bin, Kevin Huse, Christoph Wölper, and Stephan Schulz. "Synthesis and reactivity of heteroleptic zinc(i) complexes toward heteroallenes." Chemical Communications 57, no. 100 (2021): 13692–95. http://dx.doi.org/10.1039/d1cc05617d.

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Heteroleptic zinc(i) complexes Cp*Zn–ZnL1/2 were synthesized and reactions of Cp*Zn–ZnL22 with t-BuNCO and organoazides RN3 proceeded with insertion into the Zn–Zn bond and formation of novel zinc carbamate, bis-hexazene, triazenide, and azide complexes 4–7.

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17

Seck, Insa, Samba F. Ndoye, Lalla A. Ba, Alioune Fall, Abdoulaye Diop, Ismaïla Ciss, Abda Ba, et al. "Access to a Library of 1,3-disubstituted-1,2,3-triazenes and Evaluation of their Antimicrobial Properties." Current Topics in Medicinal Chemistry 20, no. 9 (May 17, 2020): 713–19. http://dx.doi.org/10.2174/1568026620666200127143005.

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Background: Due to the rapid development of microbial resistance, finding new molecules became urgent to counteract this problem. Objective: The objective of this work is to access 1,2,3-triazene-1,3-disubstituted, a class of molecule with high therapeutic potential. Methods: Here we describe the access to 17 new triazene including six with an imidazole-1,2,3-triazene moiety and eleven with an alkyl-1,2,3-triazene moiety and their evaluation against five strains: two gram (-): Escherichia coli ATCC 25921 and Pseudomonas aeruginosa ATCC 27253; two gram (+) : Staphylococcus aureus ATCC 38213 and Enterococcus faecalis ATCC 29212; and one fungi: Candida albicans ATCC 24433. Results: All strains were sensitive and the best MIC, 0.28 µM, is observed for 4c against Escherichia coli ATCC 25921. Compound 9, 3-isopropynyltriazene, appears to be the most interesting since it is active on the five evaluated strains with satisfactory MIC 0.32 µM against Escherichia coli and Pseudomonas aeruginosa and 0.64 µM against Enterococcus faecalis and Pseudomonas aeruginosa. Conclusion: Comparing the structure activity relationship, electron withdrawing groups appear to increase antimicrobial activity.

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18

Pye, Cory C., Keith Vaughan, and Julie F. Glister. "An ab initio study of conformations and sigmatropic shifts in triazene and its mono-, di-, and trimethyl derivatives." Canadian Journal of Chemistry 80, no. 5 (May 1, 2002): 447–54. http://dx.doi.org/10.1139/v02-049.

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A computational study of triazene, methyltriazene, dimethyltriazene, and trimethyltriazene is presented. A number of different conformers are analyzed and rationalized using hyperconjugation and steric interaction arguments. The transition states for rotation, inversion, and proton and methyl shifts (including water-mediated) are found and the barriers determined.Key words: triazene, ab initio, methyltriazene, 1,3-proton shift.

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19

Doucet, Katherine G., Julie F. Glister, and Cory C. Pye. "An ab initio study of model triazene-based anticancer agents." Canadian Journal of Chemistry 88, no. 8 (August 2010): 709–15. http://dx.doi.org/10.1139/v10-023.

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A computational study of a series of model triazene-based anticancer agents based on methyl- and amidyl-substituted 5-(1-triazenyl)imidazoles has been carried out, including the drugs Dacarbazine, Temozolomide, and Mitozolomide. A number of different conformers are analyzed. The transition states for the gas-phase and water-mediated triazene tautomerization reaction are found and the barriers are determined.

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20

Lerner, Hans-Wolfram, Inge Sänger, Kurt Polborn, Michael Bolte, and Matthias Wagner. "Synthese der Amide M[N(SiMetBu2)(SitBu3)] (M = Li, Na) durch N2-Eliminierung aus den Triazeniden M[tBu3SiNNNSiMetBu2] (M = Li, Na) / Synthesis of the Amides M[N(SiMetBu2)(SitBu3)] (M = Li, Na) by N2-Elimination Reaction of the Triazenides M[tBu3SiNNNSiMetBu2] (M= Li, Na)." Zeitschrift für Naturforschung B 62, no. 10 (October 1, 2007): 1285–90. http://dx.doi.org/10.1515/znb-2007-1009.

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The thermolabile triazenides M[tBu3SiNNNSiMetBu2] (M = Li, Na) are accessible from the reaction of tBu2MeSiN3 with the silanides MSitBu3 (M = Li, Na) at −78 °C in THF. At r. t. N2 elimination from the triazenides M[tBu3SiNNNSiMetBu2] (M = Li, Na) takes place with the formation of M[N(SiMetBu2)(SitBu3)] (M = Li, Na). X-Ray quality crystals of Li(THF)[N(SiMetBu2)(SitBu3)] (orthorhombic, Pna21) are obtained from a benzene solution at ambient temperature. In contrast to the structures of the unsolvated silanides MSitBu3 (M = Li, Na), the THF adduct Li(THF)3SitBu3 is monomeric in the solid state (orthorhombic, Pna21).

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21

Moser, Shasta Lee, and Keith Vaughan. "Synthesis and characterization of a series of 4-methyl-1-[2-aryl-1-diazenyl]-1,4-diazepanes and 1,4-di-[2-aryl-1-diazenyl]-1,4-diazepanes." Canadian Journal of Chemistry 82, no. 12 (December 1, 2004): 1725–35. http://dx.doi.org/10.1139/v04-153.

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1-Methylhomopiperazine was coupled with a series of diazonium salts to afford the 4-methyl-1-[2-aryl-1-diazenyl]-1,4-diazepanes (6), a new series of triazenes. These compounds are, in the main, stable crystalline solids (some of the series are stable oils), and they have been characterized by 1H and 13C NMR spectroscopy, IR spectroscopy, and mass spectrometry. NMR assignments were determined by 2D NMR and variable-temperature NMR experiments and by comparison with model compounds. A second series of new compounds, namely, 1,4-di-[2-aryl-1-diazenyl]-1,4-diazepanes (5), were prepared by coupling unsubstituted homopiperazine (1,4-diazepane) with 2 molar equivalents of the diazonium salt and were similarly characterized. The crystal and molecular structure of the parent member of this bis-triazene series (5, X = H) has been determined by single-crystal X-ray diffraction analysis.Key words: triazene, bis-triazene, diazenyl, bis-diazenyl, diazonium salt, NMR, diazepane.

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22

Alexander, Sean G., Marcus L. Cole, Craig M. Forsyth, Samantha K. Furfari, and Kristina Konstas. "Bulky triazenide complexes of alumino- and gallohydrides." Dalton Transactions, no. 13 (2009): 2326. http://dx.doi.org/10.1039/b817397d.

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23

Virag, Andrej, Anton Meden, Marijan Kočevar, and Slovenko Polanc. "Synthesis and Characterization of New Triazenide Salts†." Journal of Organic Chemistry 71, no. 10 (May 2006): 4014–17. http://dx.doi.org/10.1021/jo060178p.

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24

Alaoui, K., Y. El Kacimi, M. Galai, H. Serrar, R. Touir, S. Kaya, C. Kaya, and M. Ebn Touhami. "New triazepine carboxylate derivatives: correlation between corrosion inhibition property and chemical structure." International Journal of Industrial Chemistry 11, no. 1 (January 4, 2020): 23–42. http://dx.doi.org/10.1007/s40090-019-00199-5.

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AbstractIn this investigation, attempts have been made to study the corrosion inhibition properties of three new triazepine carboxylate compounds for mild steel in 1.0 M hydrochloric acid medium. The evaluation was carried out using mass loss, electrochemical impedance spectroscopy and polarization curves measurement. Impedance diagrams and Bode plots for uninhibited and inhibited systems were analyzed using Zview program. The fitted data observed trails in nearly the same pattern as the experimental results. It is showed that triazepine carboxylate compounds are very good inhibitors for mild steel corrosion in 1.0 M hydrochloric acid medium which act as mixed-type inhibitors. So, the inhibition efficiency was increased with inhibitor concentration in the order Cl–Me–CN > Me–CN > Cl–Me–CO2Et which depended on their molecular structures. Electrochemical impedance spectroscopy showed that all compounds act by the formation of a protective film at the metal surface. Surface analyses via SEM and Optical 3D profilometry were used to investigate the morphology of the steels before and after immersion in 1.0 M HCl solution containing inhibitors. The correspondence between inhibition property and molecular structure of the triazepine carboxylate compounds was investigated, using density functional theory (DFT). Experimental and DFT study was further supported by molecular dynamic simulations study.

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25

Lu, Guan-Han, Tzu-Chia Huang, Hsiao-Chin Hsueh, Shin-Cherng Yang, Ting-Wei Cho, and Ho-Hsuan Chou. "Novel N-transfer reagent for converting α-amino acid derivatives to α-diazo compounds." Chemical Communications 57, no. 39 (2021): 4839–42. http://dx.doi.org/10.1039/d1cc01285a.

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26

Liu, Lang, Mengyao She, Jun Zhang, Zhaohui Wang, Hua Liu, Mi Tang, Ping Liu, Shengyong Zhang, and Jianli Li. "A practical strategy for construction and regulation of multi-functional triazepinium salts via highly efficient I2-catalyzed cyclization." Green Chemistry 22, no. 10 (2020): 3111–16. http://dx.doi.org/10.1039/c9gc04328d.

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Developing a highly efficient I₂-catalyzed cyclization for constructing triazepine derivatives, which have excellent solid-state fluorescence performances, and analyzing the structure–property relationship.

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27

Fesenko, Anastasia A., Mikhail S. Grigoriev, and Anatoly D. Shutalev. "A convenient stereoselective access to novel 1,2,4-triazepan-3-ones/thiones via reduction or reductive alkylation of 7-membered cyclic semicarbazones and thiosemicarbazones." Organic & Biomolecular Chemistry 16, no. 43 (2018): 8072–89. http://dx.doi.org/10.1039/c8ob01766b.

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Stereoselective syntheses of 1-unsubstituted and 1-alkylsubstituted 1,2,4-triazepane-3-thiones/ones based on reduction or reductive alkylation of 2,4,5,6-tetrahydro-3H-1,2,4-triazepine-3-thiones/ones are reported.

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28

Abdel-Razik, H. H. "Synthesis of 1,3,5-triazepine-2,4-dione, pyrrolo[3,4-f][1,3,5]triazepine-2,4-dione, pyridazino[4,5-f][1,3,5]triazepine and 1,3,5,7,9-pentazaheptaline derivatives." Arkivoc 2004, no. 1 (May 17, 2004): 71–78. http://dx.doi.org/10.3998/ark.5550190.0005.106.

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29

Mohamed, Shaaban K., and A. M. Nour El-Din. "Solid State Photolysis of Triazene 1 -Oxides with Naphthols. Synthesis of Azo Dyes." Journal of Chemical Research 23, no. 8 (August 1999): 508–9. http://dx.doi.org/10.1177/174751989902300827.

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30

Xu, Lijun, Zhubo Liu, Weipeng Dong, Jinyu Song, Maozhong Miao, Jianfeng Xu, and Hongjun Ren. "Copper-free arylation of 3,3-disubstituted allylic halides with triazene-softened aryl Grignard reagents." Organic & Biomolecular Chemistry 13, no. 22 (2015): 6333–37. http://dx.doi.org/10.1039/c5ob00594a.

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31

Wang, Qi, Tian Lu, Chenbin Wang, Guijuan Fan, Hongquan Yin, and Fu-Xue Chen. "Synthesis of 5,5′-azoxybistetrazole via nitration and de-oxygen rearrangement of triazene." New J. Chem. 41, no. 20 (2017): 11512–16. http://dx.doi.org/10.1039/c7nj02724a.

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32

Cartei, G., V. Ceschia, M. Casasola, T. Giraldi, A. Sibau, and M. Sanzari. "Triazene (DTIC) hepatotoxicity (HPT)." Melanoma Research 3, no. 1 (March 1993): 37. http://dx.doi.org/10.1097/00008390-199303000-00126.

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33

Vassilev, Vassil, Svetlana Simova, and Blagoy Blagoev. "Triazene Derivatives of Cytisine." Archiv der Pharmazie 318, no. 7 (1985): 669–71. http://dx.doi.org/10.1002/ardp.19853180721.

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34

Nevěčná, Taťjana, Oldřich Pytela, Miroslav Ludwig, and Jaromír Kaválek. "Solvent effects on kinetics and mechanism of acid-catalyzed decomposition of 1,3-bis(4-methylphenyl)triazene I. Reactions in alcohols." Collection of Czechoslovak Chemical Communications 55, no. 1 (1990): 147–55. http://dx.doi.org/10.1135/cccc19900147.

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The effect of protic solvents (methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, cyclohexanol) has been studied on the kinetics and mechanism of acid-catalyzed decomposition of 1,3-bis(4-methylphenyl)triazene, using trichloroacetic acid as the acid catalyst. Both the non-dissociated acid and the proton have been found to be catalytically active. The mechanism of splitting of the triazene substrate with the non-dissociated acid involves the general acid catalysis. Comparison of the catalytic rate constants of the two acid catalysts and effect of solvents on these values indicate that the general acid catalysis probably also operates in the reaction of the substrate with proton.

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35

Ludwig, Miroslav, and Miriam Kabíčková. "Kinetics and Mechanism of Acid-Catalyzed Decomposition of 1,3-Bis(4-methylphenyl)triazene in Hexane-Organic Acid Medium." Collection of Czechoslovak Chemical Communications 61, no. 3 (1996): 355–63. http://dx.doi.org/10.1135/cccc19960355.

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The kinetics of acid-catalyzed decomposition of 1,3-bis(4-methylphenyl)triazene have been studied in mixtures of hexane and organic acid of various ratios using acetic, isovaleric, and pivalic acids as the catalysts. In all the cases, a monotonously increasing dependence of the observed rate constant upon mol fraction of the acid has been found. The results obtained are discussed with the help of the classic third- and fourth-order functions by Margules and the respective kinetic model. The main catalyzing particle appears to be the dimer of the respective acid, the reaction probably going via a complex formed by two molecules of acid and one molecule of the triazene.

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36

Amiri, Nayereh, Mohammad K. Rofouei, and Jahan B. Ghasemi. "Multivariate optimization, preconcentration and determination of mercury ions with (1-(p-acetyl phenyl)-3-(o-methyl benzoate)) triazene in aqueous samples using ICP-AES." Analytical Methods 8, no. 5 (2016): 1111–19. http://dx.doi.org/10.1039/c5ay03169a.

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37

Karadayı, Nevzat, Şükriye Çakmak, Mustafa Odabaşoğlu, and Orhan Büyükgüngör. "1,3-Bis(4-methylphenyl)triazene, 1-(4-chlorophenyl)-3-(4-fluorophenyl)triazene and 1-(4-fluorophenyl)-3-(4-methylphenyl)triazene." Acta Crystallographica Section C Crystal Structure Communications 61, no. 5 (April 23, 2005): o303—o305. http://dx.doi.org/10.1107/s0108270105004373.

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38

Angulakshmi, N., R. Baby Dhanalakshmi, Murugavel Kathiresan, Yingke Zhou, and A. Manuel Stephan. "The suppression of lithium dendrites by a triazine-based porous organic polymer-laden PEO-based electrolyte and its application for all-solid-state lithium batteries." Materials Chemistry Frontiers 4, no. 3 (2020): 933–40. http://dx.doi.org/10.1039/c9qm00707e.

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39

Vinduš, Denis, and Mark Niemeyer. "Hetero- and Homoleptic Magnesium Triazenides." Inorganics 5, no. 2 (May 1, 2017): 33. http://dx.doi.org/10.3390/inorganics5020033.

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40

Beweries, Torsten, Fabian Reiß, Julia Rothe, Axel Schulz, and Alexander Villinger. "Triazenido Complexes of Titanocene(III)." European Journal of Inorganic Chemistry 2019, no. 14 (April 4, 2019): 1993–98. http://dx.doi.org/10.1002/ejic.201801272.

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41

Leger, Claus-Dieter, and Gerhard Maas. "Dinuclear Ruthenium(I)Triazenide Complexes as Catalysts for Carbenoid Cyclopropanation Reactions." Zeitschrift für Naturforschung B 59, no. 5 (May 1, 2004): 573–78. http://dx.doi.org/10.1515/znb-2004-0516.

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Abstract The ability of ruthenium(I) triazenide complexes [Ru(CO)3(ArNNNAr)]2 (Ar = C6H4-4-X, X = CH3, Cl, Br) to catalyze the cyclopropanation of alkenes with methyl diazoacetate is investigated. With terminal alkenes (styrene, ethyl vinyl ether, 1-hexene), the cyclopropanecarboxylic esters are formed in good to high yield and with an E : Z diastereoisomer ratio of about 1.0 in most cases. 2-Methyl-2-butene is cyclopropanated in low yield but with a syn-selectivity up to 90:10.

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42

Martins, Marcos A. P., Paulo R. S. Salbego, Guilherme A. de Moraes, Caroline R. Bender, Priscilla J. Zambiazi, Tainára Orlando, Anderson B. Pagliari, Clarissa P. Frizzo, and Manfredo Hörner. "Understanding the crystalline formation of triazene N-oxides and the role of halogen⋯π interactions." CrystEngComm 20, no. 1 (2018): 96–112. http://dx.doi.org/10.1039/c7ce02015e.

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43

Aly, Ashraf A., Ahmed M. NourEl-Din, Mohsen A. M. Gomaa, and Magda S. Fahmi. "Rapid and Facile Synthesis of 4-Aryl-5-imino-3-phenyl-1H-naphtho[2,3-f]-1,2,4-triazepine-6,11-diones via the Reaction of Amidrazones with Dicyanonaphthoquinone." Zeitschrift für Naturforschung B 63, no. 2 (February 1, 2008): 223–28. http://dx.doi.org/10.1515/znb-2008-0217.

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One-pot syntheses of various 4-aryl-5-imino-3-phenyl-1H-naphtho[2,3- f ]-1,2,4-triazepine-6,11- diones 5a - f via reaction of amidrazones 1a - f with 1,4-dioxo-1,4-dihydronaphthalene-2,3- dicarbonitrile (4) are reported

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44

Lafrance, Ronald J., Hartford W. Manning, and Keith Vaughan. "Open-chain nitrogen compounds. Part XII. Methanolysis of 3-alkyl-3,4-dihydro-1,2,3-benzotriazin-4-ols: evidence for ring-chain tautomerism with the cytotoxic monoalkyltriazenes." Canadian Journal of Chemistry 65, no. 2 (February 1, 1987): 292–97. http://dx.doi.org/10.1139/v87-048.

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A series of 4-hydroxy-3,4-dihydro-1,2,3-benzotriazines ("triazinols"), potential pro-drugs for the cytotoxic monoalkyltriazenes, have been investigated for anti-tumor activity and have been found to have marginal activity against the TLX5 tumor. The in vivo anti-tumor activity correlates with previously observed in vitro cytotoxicity of the compounds. The chemical behaviour of the triazinols is consistent with carbinolamine [Formula: see text] triazene ring-chain tautomerism in solution. The triazinols undergo methanolysis to give a series of new 4-methoxytriazines; the rate of methanolysis is primarily dependent on the substituent at C-4 of the triazinol. Those triazinols that undergo methanolysis rapidly are also more active biologically, suggesting that cytotoxicity and anti-tumor activity derive from the insitu generation of the open chain triazene.

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45

Vaughan, Keith, Hartford W. Manning, Marcus P. Merrin, and Donald L. Hooper. "Open chain nitrogen compounds. Part XIII. 1-Aryl-3-arylthiomethyl-3-methyltriazenes and 3-(arylazo)-1,3-thiazolidines." Canadian Journal of Chemistry 66, no. 10 (October 1, 1988): 2487–91. http://dx.doi.org/10.1139/v88-391.

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Reaction of 3-acetoxymethyl-1-aryl-3-methyltriazenes with sodium thiophenolate or thiocresolate in anhydrous dimethylformamide affords a new series of 3-arylthiomethyltriazenes (2), Ar-S-CH2-NMe-N=N-Ar′. These triazenes are remarkably labile in aqueous buffer and may be good pro-drugs for the active metabolite of the antitumour dimethyltriazenes. The reaction of arenediazonium fluoroborates with 1,3-thiazolidine in aqueous acetone affords a new series of N-arylazo-1,3-thiazolidines (4); the arylazothiazolidines represent a new class of triazene in which the N3 nitrogen is incorporated into a heterocyclic unit, in this case a 1,3-thiazolidine. Nuclear magnetic resonance spectra of the arylazothiazolidines show evidence for rotational isomerism of the exocyclic N2—N3 bond in the triazene moiety.

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46

Wang, Qi, Fuqing Pang, Guilong Wang, Jinglun Huang, Fude Nie, and Fu-Xue Chen. "Pentazadiene: a high-nitrogen linkage in energetic materials." Chemical Communications 53, no. 15 (2017): 2327–30. http://dx.doi.org/10.1039/c6cc08179g.

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47

Soussi, Khaled, Shashank Mishra, Erwann Jeanneau, Jean-Marc M. Millet, and Stéphane Daniele. "Asymmetrically substituted triazenes as poor electron donor ligands in the precursor chemistry of iron(ii) for iron-based metallic and intermetallic nanocrystals." Dalton Transactions 46, no. 38 (2017): 13055–64. http://dx.doi.org/10.1039/c7dt02755a.

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48

Connelly, Neil G., Owen D. Hayward, Phimphaka Klangsinsirikul, and A. Guy Orpen. "Novel dicarbonyl and carbonylnitrosyl tris(µ-triazenide) dirhodium complexes." Journal of the Chemical Society, Dalton Transactions, no. 3 (December 17, 2001): 305–6. http://dx.doi.org/10.1039/b109972h.

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49

Bardaji, Manuel, Nathan C. Brown, Aristides Christofides, and Neil G. Connelly. "Triazenide-bridged dirhodium complexes containing redox-active cyanomanganese ligands." Journal of the Chemical Society, Dalton Transactions, no. 12 (1996): 2511. http://dx.doi.org/10.1039/dt9960002511.

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50

Preusser, Silvio, Diana Kalden, Damian Bevern, Ansgar Oberheide, Helmar Görls, Wolfgang Imhof, Matthias Westerhausen, and Sven Krieck. "Potassium Salts of Asymmetrically Substituted Amidinates and a Triazenide." European Journal of Inorganic Chemistry 2019, no. 14 (March 21, 2019): 1970–78. http://dx.doi.org/10.1002/ejic.201900159.

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