I. Yavari, F. Nasiri, H. Djahaniani
Feb 22, 2005
Citations
0
Influential Citations
5
Citations
Journal
ChemInform
Abstract
Alkyl 2-(2-fluoro-anilino)-2-oxo-acetates or ethyl 2-oxo-2-(trifluoromethylanilino)-acetate undergo a multistep reaction with dialkyl acetylenedicarboxylates in the presence of triphenylphosphine to produce dialkyl 1-(2-fluorophenyl)-4-alkoxy-5-oxo-2,5-dihydro1H-pyrrole-2,3-dicarboxylates or dialkyl 4-ethoxy-5-oxo-1-[2-(trifluoromethyl)-phenyl]-2,5-dihydro-1H-pyrrole-2,3-dicarboxylates in good yields. Dynamic NMR study of dimethyl 4-ethoxy-5-oxo-1-[2-(trifluoromethyl)-phenyl]-2,5-dihydro-1H-pyrrole-2,3-dicarboxylate shows a fairly high energy barrier (ΔG ≠ = 60.9 kJ mol - 1 ) for rotation around the N-aryl single bond, which leads to an observable atropisomerism.