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Paper | Regular issue | Vol 48, No. 5, 1998, pp.893-903
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8094
Regioselective Synthesis and Spectral Characterization of Ethyl (Z)- and (E)-2-Alkylidene-4-oxothiazolidine-5-acetate Derivatives. Solvent Effects on the Z-E Isomerization

Rade Markovic* and Marija Baranac

*Faculty of Chemistry, University of Belgrade, Studentski trg 16, P.O.Box 158, 11001 Belgrade, Yugoslavia


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 α-hydrogen. The 1H NMR data indicating the presence of both geometrical isomers in primarily nonpolar media favoring the E-form are presented in terms of the solvent influence on intra- and intermolecular H-bonding and stereochemical outcome of the reaction.