An Efficient One-Pot Synthesis of 2,3-Dialkyl-1,1-Diethyl-1-(Acetylamino)-3-(1,1,1-Triphenylphosphanilidene)-1,1,2,3-Propanetetracarboxylates and Their Temperature-Dependent NMR Spectra |
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Authors: | Sakineh Asghari Azin Salimi Vali Taghipour |
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Institution: | Department of Organic Chemistry, Faculty of Chemistry , University of Mazandaran , Babolsar , Iran |
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Abstract: | Abstract Stable crystalline phosphorus ylides of 1,1-diethyl 2,3-dimethyl 1-(acetylamino)-3-(1,1,1-triphenylphosphanilidine)-1,1,2,3-propanetetracarboxylates were obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine and dialkyl acetylenedicarboxylates in the presence of diethyl acetamidomalonate as a CH-acid. These stable ylides exist in solution as a mixture of two geometrical isomers (E and Z) as a result of restricted rotation around the carbon–carbon partial double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group on the nuclear magnetic resonance (NMR) time scale at ambient temperature. The dynamic effects in the ylide moieties were investigated by 1H NMR spectra. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. |
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Keywords: | Diethyl acetamidomalonate stable phosphorous ylides dynamic 1H NMR geometrical isomers |
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