Triazene

About: Triazene is a research topic. Over the lifetime, 759 publications have been published within this topic receiving 8714 citations. The topic is also known as: Triazene cleavage & 1-triazene.

In situ formation of arenediazonium salts and aryl radicals by aprotic nitrosation of 1,3-diaryltriazenes: dual halogen abstraction from bromotrichloromethane, and radical arylation of aromatic compounds

Abstract: Nitrosation of 1,3-diaryltriazenes (XC6H4·NHN2·C6H6X; X = H, 4-Me, 4-MeO, 4-Cl, 4-NO2, 2-Me, 2-Cl, or 3-Cl) by pentyl nitrite in benzene at 80 °C, and subsequent in situ decomposition of the resulting N-nitroso-1,3-diaryltriazenes, gives biaryls (XC6H4Ph)(54–142 mol per 100 mol of triazene). 1-(4-Chlorophenyl)-3-phenyltriazene gives a mixture of 4-chlorobiphenyl (66 mol per 100 mol) and biphenyl (65 mol per 100 mol). That aryl radicals are involved follows (a) from the formation of 2-(18.5%), 3-(49.5%), and 4-(32%) t-butylbiphenyls (total yield 106 mol per 100 mol) on nitrosation of 1,3-diphenyltriazene in t-butylbenzene, and (b) from the relative extents of reaction of this nitrosated triazene with benzene and chlorobenzene (excess of an equimolar mixture; ratio 1 : 1.6, respectively). Reaction of pentyl nitrite with 1,3-diphenyltriazene in bromotrichloromethane at 15 °C gives a precipitate of benzenediazonium chloride (80 mol per 100 mol). Also formed are bromobenzene (33), chlorobenzene (21), carbon dioxide (10), and pentyl carbanilate (10) mol per 100 mol). At 50 °C the reaction gave chlorobenzene (61) and bromobenzene (49); addition of 1,1-diphenylethene led to an almost complete reversal of these proportions. These results provide another example of anomalous dual halogen abstraction from bromotrichloromethane and support the general mechanism for this type of reaction outlined in the preceding paper.

Crystal and molecular structure of 3-methyl-1-p-tolyltriazene

Abstract: Crystals of the title compound have monoclinic symmetry with a= 8.196(1), b= 8.545(2), c= 13.163(2)A, β= 112.72(2)°, and space group P21/c. For 1 088 observed independent reflections collected on a four-circle diffractometer the R-factor reached 0.063 after full-matrix least-squares refinement. The triazene unit has a double bond between N(1)and N(2) with a hydrogen atom and a methyl group both carried by N(3). A 21–22° twist about the bond joining ring to triazene helps to relieve steric hindrance. Molecules are linked by N–H ⋯ N hydrogen bonding. The preference for the tautomeric form p-CH3·C6H4·NNH-CH3 in the solid state is consistent with the behaviour in solution, as determined by n.m.r. spectroscopy.

Microencapsulated toners having shell walls of azo and/or triazene group-containing photo-and/or thermo-labile polyurethanes or polyureas to give lower fracture, and hence fixing, temperature

Abstract: A microencapsulated toner has a shell wall of an azo and/or triazene group-containing photo-and/or thermo-labile polyurethane or polyurea, and functional core material comprising a liquid mixture with a DIN 51562 kinematic viscosity at 100 deg C below 5,000 mm /s. The shell wall is mechanically and thermally stable at below 100 deg C.

Reactions of 3-aryl-1-(tetrazol-5′-yl)triazenes with some electrophiles: mercury derivatives and fragmentations: a new route to aryl diazocyanides

Abstract: Treatment of 3-aryl-1-(tetrazol-5′-yl)triazenes (4) with lead tetra-acetate resulted in a fragmentation to aryl diazocyanides. The triazenes (4) and their monomethyl derivatives when treated with mercuric acetate and phenylmercury hydroxide gave stable mercuri compounds with mercury bonded at N-3 and the tetrazole N-2′. The reaction of the triazenes with acetic anhydride resulted in acetylation of the triazene unit with fragmentation to aryl diazonium ions and 5-acetamidotetrazoles. These reactions are discussed and the 13C n.m.r. spectra of the products are analysed.

An ab initio study of model triazene-based anticancer agents

Abstract: 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, ...