I. Yavari, F. Nasiri, H. Djahaniani
Feb 1, 2005
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Influential Citations
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Journal
Phosphorus, Sulfur, and Silicon and the Related Elements
Abstract
Abstract Ethyl 2-arylamino-2-oxo-acetates undergo a complex reaction with dimethyl acetylendicarboxylate in the presence of triphenylphosphine to produce dimethyl 1-aryl-4-ethoxy-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylates in good yields. Dynamic NMR study of dimethyl 1-(2-methyl-6-nitrophenyl)-4-ethoxy-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylate shows a fairly high energy barrier (ΔG # = 95 ± 2 kJ mol− 1) for rotation around the N-aryl single bond, which leads to an observable atropisomerism.