Journal of the Chemical Society. Perkin transactions I p. 744 - 749 (1980)
Update date:2022-08-05
Topics:
Butler, Richard N.
Cunningham, Michael G.
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.
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