Regioselective synthesis and spectral characterization of ethyl (Z)- and (E)-2-alkylidene-4-oxothiazolidine-5-acetate derivatives. Solvent effects on the Z-E isomerization
Abstract
The title compounds containing an exocyclic double bond of exclusively the Z-configuration were prepared in anhydrous ethanol by the regioselective base catalyzed reaction of diethyl 2-mercaptobutanedioate with nitrile precursors possessing an acidic a-hydrogen. The H-1 NMR data indicating the presence of both geometrical isomers in primarily nonpolar media favoring the form are presented in terms of the solvent influence on intra- and intermolecular H-bonding and stereochemical outcome of the reaction.
Source:
Heterocycles, 1998, 48, 5, 893-903Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
DOI: 10.3987/COM-97-8094
ISSN: 0385-5414
WoS: 000074365700007
Scopus: 2-s2.0-0000030167
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Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Marković, R. AU - Baranac-Stojanović, Marija PY - 1998 UR - https://cherry.chem.bg.ac.rs/handle/123456789/378 AB - The title compounds containing an exocyclic double bond of exclusively the Z-configuration were prepared in anhydrous ethanol by the regioselective base catalyzed reaction of diethyl 2-mercaptobutanedioate with nitrile precursors possessing an acidic a-hydrogen. The H-1 NMR data indicating the presence of both geometrical isomers in primarily nonpolar media favoring the form are presented in terms of the solvent influence on intra- and intermolecular H-bonding and stereochemical outcome of the reaction. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Heterocycles T1 - Regioselective synthesis and spectral characterization of ethyl (Z)- and (E)-2-alkylidene-4-oxothiazolidine-5-acetate derivatives. Solvent effects on the Z-E isomerization VL - 48 IS - 5 SP - 893 EP - 903 DO - 10.3987/COM-97-8094 ER -
@article{ author = "Marković, R. and Baranac-Stojanović, Marija", year = "1998", abstract = "The title compounds containing an exocyclic double bond of exclusively the Z-configuration were prepared in anhydrous ethanol by the regioselective base catalyzed reaction of diethyl 2-mercaptobutanedioate with nitrile precursors possessing an acidic a-hydrogen. The H-1 NMR data indicating the presence of both geometrical isomers in primarily nonpolar media favoring the form are presented in terms of the solvent influence on intra- and intermolecular H-bonding and stereochemical outcome of the reaction.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Heterocycles", title = "Regioselective synthesis and spectral characterization of ethyl (Z)- and (E)-2-alkylidene-4-oxothiazolidine-5-acetate derivatives. Solvent effects on the Z-E isomerization", volume = "48", number = "5", pages = "893-903", doi = "10.3987/COM-97-8094" }
Marković, R.,& Baranac-Stojanović, M.. (1998). Regioselective synthesis and spectral characterization of ethyl (Z)- and (E)-2-alkylidene-4-oxothiazolidine-5-acetate derivatives. Solvent effects on the Z-E isomerization. in Heterocycles Pergamon-Elsevier Science Ltd, Oxford., 48(5), 893-903. https://doi.org/10.3987/COM-97-8094
Marković R, Baranac-Stojanović M. Regioselective synthesis and spectral characterization of ethyl (Z)- and (E)-2-alkylidene-4-oxothiazolidine-5-acetate derivatives. Solvent effects on the Z-E isomerization. in Heterocycles. 1998;48(5):893-903. doi:10.3987/COM-97-8094 .
Marković, R., Baranac-Stojanović, Marija, "Regioselective synthesis and spectral characterization of ethyl (Z)- and (E)-2-alkylidene-4-oxothiazolidine-5-acetate derivatives. Solvent effects on the Z-E isomerization" in Heterocycles, 48, no. 5 (1998):893-903, https://doi.org/10.3987/COM-97-8094 . .