Collect. Czech. Chem. Commun. 1980, 45, 3557-3563

1H and 13C NMR study of (X-phenyl)-5-nitro-2-furylvinyl ethers

Miloslava Dandárová, Jaroslav Kováč and Daniel Végh

Department of Organic Chemistry, Slovak Institute of Technology, 880 37 Bratislava


Reaction of 5-nitro-2-furylvinyltrimethylammonium bromide with substituted phenolates gave (E)- and (Z)-(X-phenyl)-5-nitro-2-furylvinyl ethers. The preffered s-cis and s-trans orientations of the furan ring in Z and E isomers, respectively, were determined by 1H NMR spectroscopy. To study the extent of pconjugation, 13C NMR spectra of compounds under investigation have also been measured and interpreted. Chemical shifts for ethylenic carbons and protons were correlated with Hammett σ constants.