عنوان
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Synthesis of dimethyl 1-aryl-4- ethoxy-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylates mediated by triphenylphosphine
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نوع پژوهش
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مقاله چاپشده در مجلات علمی
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کلیدواژهها
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Hindered rotation; Intramolecular Wittig reaction; Atropisomers; Acetylenic esters; Triphenylphosphine.
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چکیده
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Ethyl 2-arylamino-2-oxo-acetates undergo a complex reaction with dimethyl acetylendicarboxylate in the presence of triphenylphosphine to produce dimethyl l-aryl-4-ethoxy-5-oxo-4,5-dihydro-1H-pyrrole-2,3-dicarboxylates in good yields. Dynamic NMR study of dimethyl 1-(2-methyl-6-nitrophenyl)-4-ethoxy-5-oxo-4,5-dihydro-1H-pyrrole-2,3-dicarboxylate shows a fairly high energy barrier (∆G≠ = 95 ± 2 kJ mol-1) for rotation around the N-aryl single bond, which leads to an observable atropisomerism.
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پژوهشگران
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حوریه جهانیانی (نفر سوم)، فاروق نصیری (نفر دوم)، عیسی یاوری (نفر اول)
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