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Title
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Synthesis and dynamic NMR study of fluorinated dialkyl 2-[(tert-butylimino)-methylene]-3-[2-alkyloxy-2-oxoacetyl)-2-fluoroanilino]-succinates
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Type
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JournalPaper
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Keywords
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ketenimines, dynamic NMR, tert-butyl isocyanide
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Abstract
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The 1:1 adduct produced in the reaction between tert-butyl isocyanide and dialkyl acetylenedicarboxylates was trapped by alkyl 2-fluoro-anilino-2-oxo-acetates or ethyl 2-oxo-2-(trifluoromethylanilino)-acetate to produce functionalized ketenimines in good yields. Dynamic NMR effects were observed in the 1H NMR spectra of these compounds as a result of restricted rotation around the single bond linking the aryl group to the ketenimine system. The free energy of activation (∆G≠) for this process is 64.9-66.5 kJ mol-1.
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Researchers
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Hamid Reza Bijanzadeh (Fourth Researcher), Hoorieh Djahaniani (Third Researcher), Farough Nasiri (Second Researcher), yavari Issa (First Researcher)
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