7334-36-3Relevant academic research and scientific papers
Pd-catalyzed C-H activation/C-N bond formation: A new route to 1-aryl-1H-benzotriazoles
Kumar, Rapolu Kiran,Ali, Md Ashif,Punniyamurthy, Tharmalingam
supporting information; experimental part, p. 2102 - 2105 (2011/06/25)
A method for the C-H activation of aryl triazene compounds followed by intramolecular amination is described. It involves the use of a catalytic amount of Pd(OAc)2 that efficiently effects the cyclization to provide 1-aryl-1H-benzotriazoles at moderate temperature.
Synthesis of primary aryl amines through a copper-assisted aromatic substitution reaction with sodium azide
Markiewicz, John T.,Wiest, Olaf,Helquist, Paul
supporting information; scheme or table, p. 4887 - 4890 (2010/10/19)
(Figure Presented) A method is presented by which aryl halides and azides are converted to the corresponding primary aryl amines with copper(I) and sodium azide.
Nitrosation with Sodium Hexanitrocobaltate(III)
Stefane, Bogdan,Kocevar, Marijan,Polanc, Slovenko
, p. 7165 - 7169 (2007/10/03)
Na3Co(NO2)6 has been investigated as a new reagent for the nitrosation of various substrates containing an amino functionality. Reactions took place in an aqueous solution of the reagent. The pH of the reaction mixture remained in the range 4.3-5. Thus, hydrazides were transformed to the corresponding acyl azides, and the reactions with arenesulfonyl hydrazines afforded arenesulfonyl azides. Treatment of aromatic amines with Na3Co(NO2)6 gave 1,3-diaryltriazenes in excellent yields; coupling of the initially formed diazo compound to the electron rich aromatic ring was also observed. Nitrosation of aliphatic amines was not possible due to complex formation with the reagent.
Triazene Drug Metabolites. Part 13. The Decomposition of 3-Acyl-3-alkyl-1-aryltriazenes in Aqueous Sulfuric Acid
Carvalho, Emilia,Iley, Jim,Rosa, Eduarda
, p. 865 - 870 (2007/10/02)
The hydrolysis of 1-aryl-3-acyl-3-methyltriazenes in aqueous sulfuric acid si described.The 3-formyl derivative undergoes an acid-catalysed deacylation reaction, characterised by a monotonic rise in the pseudo-first-order rate constant ko with increasing acidity, solvent deuterium isotope effects, kH2SO4/kD2SO4, of 0.9 (at 0.95 mol dm-3 H2SO4) and 0.8 (at 2.85 mol dm-3 H2SO4) and an entropy of activation of -80 J mol-1 K-1.The 3-alkanoyl derivatives also undergo acid-catalysed decomposition involving cleavage of either the N3-C acyl bond or the N2-N3 triazene bond.Below 3 mol dm-3 H2SO4, only acyl bond cleavage is observed.At higher acidities the extent of N2-N3 bond cleavage increases.The reaction is characterised by (i) solvent deuterium isotope effects of ca. 0.6 at 2 and 5 mol dm-3 H2SO4 and ca. 0.4 at 8 mol dm-3 H2SO4, (ii) ΔS(excit.) values of -6.7 and 51 J mol-1 K-1 at 2 and 6.1 mol dm-3 H2SO4, respectively, (iii) Hammett ρ values for the substituent in the triazene N-aryl ring of -0.7 and -0.9 at 3 and 9 mol dm-3 H2SO4, respectively, and (iv) an increase in reactivity with electron donating ability of the alkyl substituent of the acyl group.The 3-trifluoroacetyl triazenes are subject to solvolysis of the neutral, as well as the protonated, substrate.The hydrolysis of the neutral substrate involves N-acyl bond cleavage and is characterised by a solvent deuterium isotope effect, kH2O/kD2O, of 2.4, and a Hammett ρ value of +0.8 for the substituent in the N-aryl ring.The reactivity of the neutral substrate diminishes with increasing acidity until 6 mol dm-3 H2SO4, beyond which acid-catalysed N-acyl bond cleavage predominates, for which the solvent isotope effect, kH2SO4/kD2SO4, is 0.8 and the Hammett ρ value -0.5.The 3-aroyl substrates suffer acid-catalysed decomposition, the extent of the N2-N3 bond cleavage process being greater than for the N-alkanoyl counterparts.The reactions are rationalised in terms of a process that involves pre-equilibrium protonation of the substrate either at the N1 triazene atom or the amide oxygen atom, followed by subsequent decomposition of the protonated substrate via either N3-C bond cleavage, involving attack of water at the amide carbonyl, or unimolecular N2-N3 bond cleavage.The relative extents of the N3-C and N2-N3 bond cleavage processes depend on the reactivity of the acyl group and the water acitivity; the higher the water activity and the more reactive the acyl group, the more deacylation is favoured.
An Unusual Sequence of Smectic Phases Formed by Members of the Homologous Series of 3-Fluoro-4-octyloxyphenyl 4-(5-Alkyl-2-thienyl)benzoates
Butcher, J. L.,Byron, D. J.,Shirazi, S. N. R.,Tajbakhsh, A. R.,Wilson, R. C.,Bunning, J. D.
, p. 327 - 343 (2007/10/02)
Nine 4-(5-n-alkyl-2-thienyl)benzoic acids have been converted into esters by reaction with 3-fluoro-4-n-octyloxyphenol.The liquid crystal properties of these esters have been investigated by thermal optical microscopy, differential scanning calorimetry, a
Etude du Comportement Photochimique de quelques Diaryl-1,3-triazenes
Julliard, Michel,Vernin, Gaston,Metzger, Jacques
, p. 456 - 466 (2007/10/02)
The photolysis of Diaryl-1,3-triazenes gives products whose structures are consistent with a cage recombination process of homolytically formed radicals and subsequent abstraction of hydrogen from the solvent molecules by arylamino radicals.In aromatic solvents, a free-radical chain process leads to the formation of products resulting from the homolytic substitution on the solvent.Quenching experiments show that singlet and triplet excited states are reactive but that intersystem crossing efficiency is low.
