Collect. Czech. Chem. Commun.
1980, 45, 3557-3563
https://doi.org/10.1135/cccc19803557
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
Abstract
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 p-π conjugation, 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.
