4‐Thiazoline‐2‐thiones. V. Kinetic<i>vs.</i>thermodynamic control of the conjugate addition at the<i>S‐ vs. N</i>‐positions to acrylonitrile and methyl acrylate

Abstract The basic catalyzed conjugate addition of the title system in methanol was found to occur at either the S‐ or N ‐atoms, or concurrently at the S‐ and N ‐atoms, of the magnified image moiety of the heterocycle. Evidence indicates that the formation of the two types of adducts depends on an equilibrium between the reactions of conjugate addition and reversal. Certain choice of isolation of the two types of products is allowed by control of the reaction conditions.

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