Study of E/Z isomerization of (arylamino)methylidenefuran-2(3H)-ones by1H,13C,15N spectroscopy and DFT calculations in different solvents.
The structure and configuration of the series of previously unknown arylaminomethylidenefuran-2(3H)-ones have been determined in solution by1H,13C,15N nuclear magnetic resonance spectroscopy including two-dimensional experiments such as1H─1H COSY, dqCOSY,1H─13C HSQC,1H─13C HMBC. It was found that synthesized substances exist as an equilibrium mixture of E- and Z-enamines in solution. It was established on the basis of density functional theory calculations that the exchange between the two push-pull enamines is a simple rotation around an exocyclic partial double bond that depends on the effect of the solvents. Copyright © 2017 John Wiley & Sons, Ltd.
Alexander K
http://orcid.org/0000-0001-8682-4569
AK
Osipov
Institute of Chemistry, National Research Saratov State University, Astrakhanskaya St., 83, Saratov, 410012, Russia.
Alexander A
http://orcid.org/0000-0002-6459-1511
AA
Anis'kov
Institute of Chemistry, National Research Saratov State University, Astrakhanskaya St., 83, Saratov, 410012, Russia.|Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Prospekt Entuziastov, Saratov, 410049, Russia.
Vyacheslav S
http://orcid.org/0000-0002-0627-6804
VS
Grinev
Institute of Chemistry, National Research Saratov State University, Astrakhanskaya St., 83, Saratov, 410012, Russia.
Alevtina Yu
http://orcid.org/0000-0002-4368-0021
AY
Yegorova
E/Z isomerization; arylaminomethylene derivatives of furanones; condensation; configuration; furan-2(3H)-ones; push-pull olefins; triethyl orthoformate