Study of E/Z isomerization of (arylamino)methylidenefuran‐2(3H)‐ones by 1H, 13C, 15N spectroscopy and DFT calculations in different solvents. (20th March 2017)

• Record Type: Journal Article
• Authors: Osipov, Alexander K.; Anis'kov, Alexander A.; Grinev, Vyacheslav S.; Yegorova, Alevtina Yu.
• Is Part Of: Magnetic resonance in chemistry. Volume 55:Number 8(2017:Aug.)
• Page Start: 730
• Page End: 737
• Publication Date: 2017-03-20
• Subjects: furan‐2(3H)‐ones -- E/Z isomerization -- configuration -- triethyl orthoformate -- push–pull olefins -- arylaminomethylene derivatives of furanones -- condensation; Nuclear magnetic resonance spectroscopy -- Periodicals; Chemistry, Organic -- Periodicals; Magnetic resonance -- Periodicals; 538.36
• DOI: 10.1002/mrc.4583
• Languages: English
• ISSNs: 0749-1581

Abstract

Abstract : The structure and configuration of the series of previously unknown arylaminomethylidenefuran‐2(3 H )‐ones have been determined in solution by 1 H, 13 C, 15 N nuclear magnetic resonance spectroscopy including two‐dimensional experiments such as 1 H─ 1 H COSY, dqCOSY, 1 H─ 13 C HSQC, 1 H─ 13 C 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. Abstract : E/Z isomerization of (arylamino)methylidenefuran‐2( 3H )‐ones was studied by 1 H, 13 C, 15 N spectroscopy. It was established on the basis of DFT 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.