Synthesis of the H-phosphonate dibenzo[d, f][1, 3, 2]dioxaphosphepine 6-oxide and the phospha-Michael addition to unsaturated compounds. Issue 9 (1st March 2019)

• Record Type: Journal Article
• Authors: Lenz, Johannes; Pospiech, Doris; Komber, Hartmut; Paven, Maxime; Albach, Rolf; Mentizi, Stamo; Langstein, Gerhard; Voit, Brigitte
• Is Part Of: Tetrahedron. Volume 75:Issue 9(2019)
• Page Start: 1306
• Page End: 1310
• Publication Date: 2019-03-01
• Subjects: Alkene -- 2, 2′-Biphenol -- Phosphonate -- Phospha-Michael addition; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.01.045
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A series of phosphonate-containing compounds based on dibenzo[ d, f ][1, 3, 2]dioxaphosphepine 6-oxide (BPPO) is presented. BPPO is synthesized by a three–component condensation and is added to activated alkenes with systematically varied structure via phospha-Michael addition. Acrylates, α, β-unsaturated carboxylic acid diesters and benzoquinone are used as activated alkenes. The new compounds are characterized by 1 H, 13 C and 31 P NMR spectroscopy. The as-prepared phosphonates are envisioned to have flame retardant properties. Graphical abstract: Image 1