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From Phosphonic Acid to O–P Heterocycles Using MW: An Access to [5]-, [6]- and [8]-Membered Annelated Phosphinates

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Abstract

In this work, we describe the synthesis of O,P-heterocycles with sizes of 5, 6 and 8 atoms. A one pot-two steps processes accounts for the preparation of 1,2-oxaphosphinane and 1,2-oxaphosphacane. The synthesis of 1,2-oxaphospholane requires two steps involving the installation of functional group on the phosphinate introducing a P-O bond followed by the formation of a Pd-catalyzed C-P bond formation. Their molecular structures were assessed by single crystal X-ray diffraction. The geometries of the studied compounds were optimized using density functional theory (DFT) at the B3LYP and M06-2X hybrid functionals and compared to the experimental solid state data. In addition, Hirchfeld surfaces and frontier molecular orbitals were described.

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Authors and Affiliations

  1. Université Paris-Saclay, UVSQ, CNRS, Institut Lavoisier de Versailles, 78035, Versailles, France

    S. Azzouni, A. Gaucher, J. Marrot & D. Prim

  2. Laboratory of Heterocyclic and Selective Organic Chemistry, Department of Chemistry, Faculty of Sciences of Tunis, University of Tunis El Manar, 2092, Tunis, Tunisia

    S. Azzouni & M. L. Efrit

  3. Laboratory of Caracterisations, Applications and Modeling of Materials LR18ES08, Faculty of Sciences of Tunis, University of Tunis El Manar, 2092, Tunis, Tunisia

    S. Hassen & Y. Arfaoui

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  1. S. Azzouni
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Azzouni, S., Gaucher, A., Hassen, S. et al. From Phosphonic Acid to O–P Heterocycles Using MW: An Access to [5]-, [6]- and [8]-Membered Annelated Phosphinates. Chemistry Africa 7, 1187–1199 (2024). https://doi.org/10.1007/s42250-023-00816-y

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