A Simple Synthesis of Stable Phosphoranes Derived from Imidazole Derivatives |
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Authors: | Malek Taher Maghsoodlou Sayyed Mostafa Habibi Khorasani Nourollah Hazeri Mahmoud Nassiri Reza KaKaei Ghasem Marandi |
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Institution: | Department of Chemistry , The University of Sistan and Baluchestan , Zahedan, Iran |
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Abstract: | Stable crystalline phosphorus ylides were obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, in the presence of strong NH-acids, such as imidazole, 2-methylimidazole, 4-methylimidazole, 2-ethylimidazole, benzimidazole, and 5,6-dimethylbezimidazole. These stable ylides exist in solution as a mixture of two geometrical isomers as a result of restricted rotation around the carbon–carbon partial double bond resulting from the conjugation of the ylide moiety with the adjacent carbonyl group. |
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Keywords: | Acetylenic ester NH-acids stable phosphorus ylides triphenylphosphine |
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