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2 - [2 - (η ~ 5 - cyclopentadienyl -yl) ethyl ] - 1H - imidazole ligand and titanium ( IV ) Synthesis , structure and catalytic activity

Author: GeFang
Tutor: NieWanLi
School: Northwestern University
Course: Organic Chemistry
Keywords: Imidazole Cyclopentadienyl ligands Titanium Hydrogen amination The catalytic ethylene (co) polymerization
CLC: O641.4
Type: Master's thesis
Year: 2010
Downloads: 27
Quote: 1
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Abstract


The laboratory recently synthesized a series of novel substituted cyclopentadienyl 2 - (1H-imidazol -2 -) ethyl ligand and its complexes with a transition metal of the fourth sub-group Synthesis, Structure and The performance further research. In this thesis, improved synthetic routes and purification methods of synthesis of such ligands in the lab before. Reaction by the lithiated 1-N-(diethoxy-methyl) -2 - methyl-1H-imidazole (1) after reaction with the corresponding fulvene, then its acid solution under mild conditions, and, to give the corresponding ligands 2 - cyclopentadienyl -2,2 - diphenyl-ethyl-1H-imidazole (2a), 2 - cyclopentadienyl -2 - phenyl-ethyl-1H-imidazole (2c) and 2 - cyclopentadienyl -2 - methyl-propyl-1H-imidazole (2b). Obtained in the process of the purified ligand 2c dimer rac-3, 5 - di-(1RS-2-phenyl-methyl-1H-imidazolyl) -4,7 - methylene-the bridging-1H-inden (2c '). The crystal and molecular structure of the polymer (2c ') are characterized by single-crystal X-ray diffraction analysis. Ligands 2a and 2b, respectively, with the Ti (NET2) 4 at 80 ° C in toluene to give (2 - cyclopentadienyl -2,2 - diphenyl-ethyl-1H-imidazol) - bis (N, N - diethylamino) titanium (IV) 3A and (2 - cyclopentadienyl -2 - methyl-propyl-1H-imidazol) - bis (N, N-diethylamino) titanium (IV) 3b, and by X-ray single crystal diffraction analysis verified the structure of the complexes 3b. Complexes 3a and 3b are reacted with an excess of trimethylsilyl chloride to give the dichloro-(2 - cyclopentadienyl -2,2 - diphenyl-ethyl-1H-imidazol) titanium (IV) (8a) and tri- chloro-(2 - cyclopentadienyl -2 - methyl-propyl-1 - (trimethylsilyl)-1H-imidazole) titanium (IV), (6b '). 6b 'crystals were analyzed by X-ray diffraction. Only the presence of an excess of trimethylchlorosilane compound 6b 'to stabilize in solution. In addition, it can be seen from the NMR data, the solution containing 15 mol% of another product dichloro-[2 - cyclopentadienyl -2 - methyl-propyl-1H-imidazole] titanium (IV) 6b Compound 6b 'and 6b to each other in solution equilibrium conversion. All organic and metal structures of organic compounds have been characterized by 1H and 13C NMR analysis. With the titanium material 3a, 3b carried hydrogen amination catalytic activity, but the effect is not ideal. In addition, the titanium complex 3b of the catalytic polymerization of ethylene, of polymerization activity, and its catalytic activity is not high. 'Catalytic ethylene polymerization activity found in the Al / Ti molar ratio constant, catalytic temperature and time change has little effect on the catalytic effect of compound 6b.

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