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Title
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Synthesis and Dynamic NMR Study of Ketenimines Derived from tert-Butyl Isocyanide, Alkyl 2-Arylamino-2-oxo-acetates, and Dialkyl Acetylenedicarboxylates
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Type
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JournalPaper
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Keywords
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Ketenimines, tert-Butyl isocyanide, Peri-interaction, Hindered rotation,Three-component reaction, Ugi reaction
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Abstract
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The adduct produced in the reaction between tert-butyl isocyanide and dialkyl acetylenedicarboxylates was trapped by alkyl 2-arylamino-2-oxo-acetates. When the aryl group is 2-methyl-6-nitrophenyl or 2,6-di-isopropylphenyl, the product exists as two stable rotamers at room temperature as a result of restricted rotation around the Ar-N single bond. When the aryl group is 1-naphthyl or 8-quinolinyl, dynamic NMR effects are observed in the 1H NMR spectra. The calculated free-energy of activation for interconversion of the rotational isomers in 1-naphthyl and 8-quinolinyl derivatives amounts to about 99+/-2 and 68.5+/-2 kJ mol(-1), respectively.
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Researchers
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Hoorieh Djahaniani (Third Researcher), Farough Nasiri (Second Researcher), yavari Issa (First Researcher)
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