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4‐Thiazoline‐2‐thiones. V. Kinetic vs. thermodynamic control of the conjugate addition at the S‐ vs. N ‐positions to acrylonitrile and methyl acrylate
Author(s) -
Humphlett W. J.
Publication year - 1968
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570050313
Subject(s) - chemistry , conjugate , thiazoline , moiety , acrylonitrile , methyl acrylate , adduct , medicinal chemistry , kinetic energy , addition reaction , methanol , acrylate , kinetic control , polymer chemistry , catalysis , stereochemistry , organic chemistry , polymer , copolymer , mathematical analysis , quantum mechanics , physics , mathematics
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 themoiety 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.