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通过间苯二甲醛与5-氟苯基二吡咯甲烷反应合成了一种新的间位苯基桥联的双咔咯1,并利用锰盐与自由咔咯反应制备了其锰的金属配合物2。采用紫外、质谱、核磁、XPS等手段对化合物进行了表征。以苯乙烯为底物考察了锰双咔咯2的催化氧化性质,探讨了时间、溶剂、氧源、轴向配体对催化反应的影响。结果表明以亚碘酰苯和间氯过氧苯甲酸为氧源时催化的主要产物为环氧苯乙烷,而以双氧水和叔丁基过氧化氢为氧源时则主要产物为苯甲醛;在极性溶剂中的催化氧化产率较高。轴向配体对催化氧化有促进作用,不同轴向配体对催化反应产率提高的顺序是:1-甲基咪唑>吡啶>咪唑。
A new meta-bridged bis-carbazole 1 was synthesized by the reaction of isophthalaldehyde with 5-fluorophenyldipyrromethane and its manganese complex was prepared by the reaction of manganese salt with free carbazole 2. The compounds were characterized by UV, MS, NMR and XPS. The catalytic oxidation of manganous biscarbazole 2 was investigated by using styrene as substrate. The effects of time, solvent, oxygen source and axial ligand on the catalytic reaction were investigated. The results showed that the main product catalyzed by iodosylbenzene and m-chloroperoxybenzoic acid was epoxybenzene, while the main product was benzaldehyde with hydrogen peroxide and t-butyl hydroperoxide as oxygen source. The catalytic oxidation in polar solvents yields a higher yield. The axial ligand promoted the catalytic oxidation. The order of the increase of the catalytic reaction yield of different axial ligands was: 1-methylimidazole> pyridine> imidazole.