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Synthesis of thiazol‐2‐imines from the reduction of single enantiomer 2‐imino‐thiazolidin‐4‐ones followed by a spontaneous water elimination
Author(s) -
Tuncel Senel Teke,
Dogan Ilknur
Publication year - 2020
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23197
Subject(s) - chemistry , enantiomer , reaction rate constant , dehydration , kinetics , medicinal chemistry , stereochemistry , nuclear magnetic resonance spectroscopy , elimination reaction , biochemistry , physics , quantum mechanics
Chiral hemiaminals ( 5‐8 RR and 5‐8 SS ) have been synthesized from the corresponding 2‐iminothiazolidine‐4‐ones ( 1‐4 RR and 1‐4 SS ) by LiAlH 4 reductions stereoselectively and were then converted to single enantiomer thiazol‐2‐imines ( 9‐12 RR and 9‐12 SS ) by a water elimination reaction. The kinetics of the dehydration reactions which occurred spontaneously both in the solid state and in the solution have been followed by time dependent 1 H nuclear magnetic resonance spectroscopy. The corresponding first order rate constants and free energies of activation values for the conversions have been reported.