TAUTOMERISM OF DIMETHYLHYDRAZONES OF β-DICARBONYL COMPOUNDS
A study was made of the relation of the hydrazone-enehydrazine equilibrium of dimethylhydrazones of β-diketones to the steric and electronic properties of substituents of the β-dicarbonyl component.In dimethylhydrazones of aliphatic β-diketones the hydrazone form is favored by increase in the sizes of the substituents at the C=N bond and in the α position; the proportion of the enehydrazine form rises with increase in the size of the carbonyl function.In dimethylhydrazones of aroyl-containing β-diketones a condition for the appeareance of tautomeric equilibrium is the presence of a strong electron-acceptor substituent at the C=N bond; the introduction of electron-donor substituents into the aromatic nucleus at the C=O bond shifts the equilibrium toward the hydrazone form.
Yakimovich, S. I.,Zerova, I. V.
p. 1427 - 1433
(2007/10/02)
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