Collect. Czech. Chem. Commun.
1982, 47, 3412-3417
https://doi.org/10.1135/cccc19823412
Stereochemistry of some substituted 2-furyl- and 2-thienyl ethylene derivatives. 1H NMR study
Miloslava Dandárová, Jaroslav Kováč, Daniel Végh and Vladimír Žvak
Department of Organic Chemistry, Slovak Institute of Technology, 812 37 Bratislava
Abstract
Stereochemistry of (E)- and (Z)-1-(5-nitro-2-furyl)-2-Y-ethylenes and 1-(5-nitro-2-thienyl)-2-Y-ethylenes (where Y = CH3O, 4-CH3C6H4O, N3 and Br) and of E and Z isomers of methyl 2-methyl-3-(2-furyl)propenoate and methyl 2-methyl-3-(2-thienyl)propenoate was studied by 1H NMR spectroscopy. With 1-(5-nitro-2-furyl)-2-Y-ethylenes, it was found that the preferred conformation of the furyl substituent relative to the side chain double bond is s-trans in the E isomers and s-cis in the Z isomers. The s-cis conformation is prevailing in both isomers of methyl 2-methyl-3-(2-furyl)propenoate. The E and Z isomers of all studied thiophene derivatives exist in the s-trans conformation.
