Abstract
The 13C and 15N-NMR spectra of compounds prepared by coupling benzenediazonium ions with 9-hydroxyanthracene, acetylcyclopentadiene, 8-hydroxy quino line, 3-cyano-1,4-dimethylpyridine-2,6-dione and 1-naphthol have been measured. Using δ( 13C), δ( 15N), 1J( 15NH) and 1J( 15N 15N) it has been found that the products exist, in deuterio-chloroform or in hexadeuteriodimethyl sulfoxide solutions, as 9,10-anthraquinone 9-phenylhydrazone ( I), 2-acetyl-2,4-cyclopentadienone 1-phenylhydrazone ( II), 5-phenylazo-8-hydroxyquinoline ( III), 3-cyano-1,4-dimethylpyridine-2,5,6-trione 5-phenylhydrazone ( IV) and 4-phenyl-azo-1-naphthol ( V). The compounds VI and VII have been found to be equilibrium mixtures of the azo and hydrazone tautomers, with prevailing 1,2-naphthoquinone 2-phenylhydrazone ( VI) and 4-phenylazo-1,2-naphthoquinone 2-phenylhydrazone ( VII) configurations.
Published Version
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