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Multinuclear NMR structural study of novel γ-iminophosphonate and phosphine oxide derivatives

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Abstract

We report for the first time the synthesis of γ-iminophosphonates and phosphine oxides from the acid-catalysed reaction of primary amines with γ-phosphonylketones. The full characterization of these compounds through their 1H, 31P, and 13C NMR spectra indicates that they are obtained as a mixture of Z and E isomers. An unambiguous method for the assignment of these configurations, based on the 13C chemical shifts of C2 carbon atoms in the α position with respect to the C=N double bond is used. The 31P chemical shifts are also of diagnostic importance in assigning the Z and E configurations. Indeed, the phosphorus atom is found to resonate at a slightly higher field in Z isomers.

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Authors and Affiliations

  1. Laboratory of Heteroatom Organic Chemistry, Department of Chemistry, Faculty of Sciences of Bizerta, University of Carthage, Jarzouna, Tunisia

    A. Wahbi, H. Slimani & S. Touil

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  1. A. Wahbi
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  2. H. Slimani
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  3. S. Touil
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Correspondence to S. Touil.

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Original Russian Text © 2015 A. Wahbi, H. Slimani, S. Touil.

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 56, No. 1, pp. 41–48, January–February, 2015.

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Wahbi, A., Slimani, H. & Touil, S. Multinuclear NMR structural study of novel γ-iminophosphonate and phosphine oxide derivatives. J Struct Chem 56, 34–41 (2015). https://doi.org/10.1134/S0022476615010060

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  • DOI: https://doi.org/10.1134/S0022476615010060

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