Regioselective synthesis and spectral characterization of ethyl (Z)- and (E)-2-alkylidene-4-oxothiazolidine-5-acetate derivatives. Solvent effects on the Z-E isomerization
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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, 893-903
- Pergamon-Elsevier Science Ltd, Oxford