Steric structure of alkyl 2-aryl(hetaryl)hydrazono-3-fluoroalkyl-3-oxopropionates

Steric structure of fluorinated 2-arylhydrazono-3-oxo esters was studied by 1 H, 19 F, and 13 C 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 CDCl 3 exist as Z isomers with the ester fragment involve...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2009-06, Vol.45 (6), p.801-809
Main Authors: Khudina, O. G., Burgart, Ya. V., Shchegol’kov, E. V., Saloutin, V. I., Kazheva, O. N., Chekhlov, A. N., D’yachenko, O. A.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:Steric structure of fluorinated 2-arylhydrazono-3-oxo esters was studied by 1 H, 19 F, and 13 C 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 CDCl 3 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 CDCl 3 gives rise to a mixture of Z and E isomers, the latter prevailing.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428009060013