Journal
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 45, Issue 6, Pages 801-809Publisher
MAIK NAUKA/INTERPERIODICA/SPRINGER
DOI: 10.1134/S1070428009060013
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- Russian Federation [3758.2008.3]
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Steric structure of fluorinated 2-arylhydrazono-3-oxo esters was studied by H-1, F-19, and C-13 NMR spectroscopy and X-ray analysis. It was found that these compounds in the crystalline state and in solutions in acetone-d (6), DMSO-d (6), and CDCl3 exist as Z isomers with the ester fragment involved in intramolecular hydrogen bond with the hydrazone NH proton. Exceptions are alkyl 2-arylhydrazono-4,4-difluoro-3-oxobutanoates which exist in acetone-d (6) as mixtures of Z and E isomers, the former prevailing. Unlike fluorinated analogs, ethyl 2-(4-methylphenyl)hydrazono-3-oxobutanoate in crystal has the structure of E isomer in which intramolecular hydrogen bond is formed between the NH proton and acetyl carbonyl group. The same compound in acetone-d (6), DMSO-d (6), and CDCl3 gives rise to a mixture of Z and E isomers, the latter prevailing.
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