74733-96-3Relevant articles and documents
Regioselective Intramolecular Rearrangements in 1,2-Bis(areneazo)cycloalkenes via Triazolium Imide 1,3-Dipoles: Examples of a New Fischer Indole-type Rearrangement. Azolium 1,3-Dipoles. Part 2.
Butler, Richard N.,Gillan, Ann M.,James, John P.,Evans, Ann M.
, p. 159 - 163 (2007/10/02)
1,2-Bis(areneazo)cycloalkenes (2) (6 carbons and higher) when heated or treated with acid rearrange to hydro derivatives of fused 2,4-diarylcyclopolyenotriazoles (3).The rearrangement, which was regioselective and intramolecular, occured through a 1,2,3-triazolium imide 1,3-dipole form of the substrates (2).Synthesis, structural effects, a variable-temperature 270 MHz n.m.r. search for intermediates, and some kinetic studies are reported.The reaction is a new variation of the Fischer indole reaction.
Isomerism and Lead(IV) Acetate Oxidation Reactions of p-Substituted Phenylosazones of Some Substituted Glyoxals and 1,2-Diketones. Reactions of Metallic Acetates with Nitrogen Compounds. Part 5.
Butler, Richard N.,Cunningham, Michael G.
, p. 744 - 749 (2007/10/02)
The structures of the bis-(p-nitrophenyl)hydrazones and some bis-(p-bromophenyl)hydrazones of glyoxal, methylglyoxal, phenylglyoxal, butane-2,3-dione, benzil, and cyclohexane-1,2-dione were examined by i.r., 1H n.m.r., and 13C n.m.r. spectroscopy.Generally the E,E forms of the osazones were obtained from direct synthesis except for the bis-(p-nitrophenyl)hydrazone of cyclohexane-1,2-dione and phenylglyoxal and the bis-(p-bromophenyl)hydrazones of phenylglyoxal, which were obtained as the E,Z-chelate forms.Unstable yellow crystalline forms of the bis-(p-nitrophenyl)hydrazones of glyoxal, butane-2,3-dione, and benzil containing two molecules of hexamethylphosphoramide (HMPA) of crystallisation, which may contain the E,Z-isomers, were isolated from HMPA solutions.Lead tetra-acetate oxidation of a range of E,E-osazones gave dehydrogenations to 1,2-bisazoethylenes.Similar oxidations of E,Z-osazones gave mainly 2-aryl-1,2,3-trizole type products (osotriazoles) along with lower yields of azoethylenes.Oxidation of cyclohexane-1,2-dione bis-(p-nitrophenyl)hydrazone gave a mixture of osotriazoles containing an acethoxy- or p-nitroacetanilido-group at the 3-position of the cyclohexyl ring.