Synthesis of Fluorinated Dialkyl 1-Aryl-4-alkoxy-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylates

• Autorzy: Yavari I. , Nasiri F. , Djahaniani H.
• Języki publikacji: EN

Abstrakty

EN

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 l-(2-fluorophenyl)-4-alkoxy-5-oxo-2,5-dihydro-1H-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 (DeltaG _ = 60.9 kJ mol-1) for rotation around the N-aryl single bond, which leads to an observable atropisomerism.

Słowa kluczowe

EN

hindered rotation; rotational isomers; intramolecular Wittig reaction; atropisomers; triphenylphosphine

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2004
• Tom: Vol. 78 / nr 10
• Strony: 1871--1876
• Opis fizyczny: Bibliogr. 16 poz., rys.

Twórcy

autor

Yavari I.

• Department of Chemistry, Tarbiat Modarres University, PO Box 14115-175, Tehran, Iran

autor

Nasiri F.

• Department of Chemistry, Tarbiat Modarres University, PO Box 14115-175, Tehran, IranDepartment of Chemistry, Tarbiat Modarres University, PO Box 14115-175, Tehran, Iran

autor

Djahaniani H.

• Department of Chemistry, Tarbiat Modarres University, PO Box 14115-175, Tehran, Iran

Bibliografia

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