Abstract

Using13C-NMR spectroscopy conditions have been elucidated under which 4-R-azo-1-naphthol derivatives containing carbo- and heterocyclic functional groups R exist in solution predominantly in azo- or quinonehydrazone tautomeric forms, respectively. A mechanism has been proposed to account for azo-quinonehydrazone tautomerism; this mechanism would be expected to be valid in aprotic meida for hydroxyazo compounds which do not contain intramolecular hydrogen bonds.

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