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UBC Theses and Dissertations

Synthesis, polymerization and metal binding studies of new phosphaalkenes bearing donor substituents Juilfs, Amber Michelle


A new P-Mes (Mes = 2,4,6-trimethylphenyl) phosphaalkene bearing a chelating C-substitutent has been prepared: MesP=C(Ph)(o-DMA) (o-DMA = orthodimethylaniline) (1a). Phosphaalkene 1a was prepared by the standard phospha-Peterson reaction. Radical polymerization of 1a afforded [MesP-C(Ph)(o-DMA)]n (2a). Lithiation followed by protonation of 1a and previously synthesized phosphaalkene MesP=C(Ph)(2- Pyd) (2-Pyd = 2-pyridine) (2a) afforded model compounds (Mes)(Me)P-CH(Ph)(o- DMA) (3a) and (Mes)(Me)P-CH(Ph)(2-Pyd) (3b), respectively. Model compounds 3a and 3b were complexed to Pd(II) resulting in metal complexes (Mes)(Me)P-CH(Ph)(o-DMA)PdCl₂ (4a), [(Mes)(Me)P-CH(Ph)(o- DMA)]₂PdCl₂ (4b), and (Mes)(Me)P-CH(Ph)(2-Pyd)PdCl₂ (4c), respectively. The metal binding properties of the metal complexes were investigated by NMR spectroscopy and X-ray crystallography. The results showed that metal complex 4b coordinated Pd(II) in a two to one fashion by analysis of X-ray crystallography whereas complex 4c coordinated Pd(II) in a bidentate fashion through the phosphorus and nitrogen atoms. Crystals were not obtained for complex 4a, however NMR spectroscopy shows the complex differs from the free ligand 3a and the two to one complex 4b.

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