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Synthesis and Organo-Catalyzed Ring-Opening of a Six-Membered Heterocycle Combining Phosphonate and Ester Functions |
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| Authors: | Thasanaporn Ungpittagul Arnut Virachotikul Julien Monot Blanca Martín-Vaca Didier Bourissou |
| Affiliation: | 1. Laboratoire Hétérochimie Fondamentale et Appliquée (UMR 5069), Université de Toulouse (UPS), CNRS, 118 route de Narbonne, F-31062 Toulouse, France These two authors contributed equally to the work.;2. Laboratoire Hétérochimie Fondamentale et Appliquée (UMR 5069), Université de Toulouse (UPS), CNRS, 118 route de Narbonne, F-31062 Toulouse, France |
| Abstract: | The synthesis of a difunctional P-heterocycle combining phosphonate and ester moieties in a six-membered ring is described. Using trifluoromethane sulfonic acid HOTf as organocatalyst, ring-opening with neopentyl alcohol readily occurs with complete selectivity for O-acyl bond cleavage. In turn, ring-opening polymerization proceeds in a controlled manner when an excess of P-heterocycle is used. Copolymerization with ϵ-caprolactone is also reported and semi-batch conditions are shown to enable regular incorporation of the phosphonate moieties along the polymer chains. |
| Keywords: | P-Heterocycles Hybrid monomers Lactones Microwave heating Organocatalysis Ring-opening |