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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.

DOI: 10.1039/P19800000744

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 744 - 749 (1980)

Update date:2022-08-05

Topics:

Authors:

Butler, Richard N.Butler, Richard N.

Cunningham, Michael G.Cunningham, Michael G.

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Article abstract of DOI:10.1039/P19800000744

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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Product name:1-phenyl-1,2-bis-(p-bromophenylazo)ethylene

Cas No:74733-91-8

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