Synthesis and spectroscopic properties of rotamers in the series of 2-(fluoroaryl)-4-substituted pyrroles

•A mild, simple and efficient method for the synthesis of fluroaryl substituted pyrroles was elabotated.•All ortho-fluroaryl substituted pyrroles contains double sets signals in 13C NMR spectra.•Based on the combination of 2D HMBC and HSQC NMR spectroscopy, as well as temperature dependent NMR exper...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2021-09, Vol.249, p.109863, Article 109863
Main Authors: Miftyakhova, Almira R., Matveeva, Maria D., Zhilyaev, Dmitry I., Eltsov, Oleg S., Talarico, Giovanni, Smol'yakov, Alexander F., Voskressensky, Leonid G., Efimov, Ilya V.
Format: Article
Language:English
Subjects:
Cycloaddition
Enamine
Enaminone
Fluorine
Isocyanide
Isomers
Magnetic resonance spectroscopy
NMR
NMR spectroscopy
Nuclear magnetic resonance
Pyrrole
Pyrroles
Rotamers
Spectroscopy
Spectrum analysis
Substitutes
Synthesis
Temperature dependence
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Summary:•A mild, simple and efficient method for the synthesis of fluroaryl substituted pyrroles was elabotated.•All ortho-fluroaryl substituted pyrroles contains double sets signals in 13C NMR spectra.•Based on the combination of 2D HMBC and HSQC NMR spectroscopy, as well as temperature dependent NMR experiments in DMSO and CDCl3 we conclude that the ratio of obtained rotamers does not depends on the nature of the solvent and temperature. A mild, simple and efficient method for the synthesis of ortho, meta and para-fluoroaryl substituted pyrroles was discovered. It was found by NMR spectroscopy, that ortho-fluoroaryl substituted pyrroles exist in the form of inhibited conformational isomers (rotamers). Intramolecular interaction of the hydrogen atom of the pyrrole ring and the fluorine atom in the ortho-position of the aryl substituent leads to the appearance of two sets of signals in the 1H and 13C NMR spectra. Based on the combination of 2D HMBC and HSQC NMR spectroscopy, as well as temperature dependent NMR experiments in DMSO and CDCl3 we conclude that the ratio of obtained rotamers is permanent and does not depend from the temperature. To create your abstract, type over the instructions in the template box below. Fonts or abstract dimensions should not be changed or altered. [Display omitted]
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2021.109863