Study Of Synthesis And Properties Of Muti-Ring Compounds

1,6-methano[10]annulene is an aromatic compound with a high electron delocalization.1,6-methano[10]annulene derivatives have been found with high physical activities and electrochemical activities. They can be applied in the fields of medicine industry, pesticide and cathode materials of lithium battery. Thus, a study of the synthesis of1,6-methano[10]annulene derivatives would be important to the molecular design for new substance materials in the field of materials science.This thesis introduced an efficient and convenient method for the synthesis of anthraquinone derivatives under solvent-free conditions using ZrOCl2·-8H2O as catalyst, and phthalic anhydride(PhA) with various benzene derivatives as raw materials. We took the synthesis of1,4-dihydroxy-9,10-anthraquinone as an example in a solvent-existed reaction and a solvent-free reaction. The experimental data showed that1,4-dihydroxy-9,10-anthraquinone from mole ratio of n(ZrOCl2·8H2O)/n(PhA)=2:1 displayed an excellent yield of96%. And the yield of other anthraquinone derivatives ranged from88%to96%. This remarkable advantage was offered by ZrOCl2·8H2O as a catalyst in the Friedel-Crafts reactions.Later on, we discussed the importance of the synthesis of1,6-methano-[10]annulene-3,4-dicarboxylicanhydrideis in this thesis.1,6-methano-[10]annuleno[3,4-g]-anthraquinone derivatives were prepared by a convenient method starting from1,6-methano[10]annulene-3,4-dicarboxylic anhydride and benzene derivatives(e. g. hydroquinone, m-dihydroxybenzene, methyl-naphthohydroquinone and4-methoxyphenol) under the condition of ZrOCl2·8H2O/NaCl as catalyst at a temperature of165℃. The new compounds were characterized by IR, NMR, MS and HRMS spectra. The electrochemical properties were also investigated. The highest cycle capacity was443.0mAh·g-1, which indicated that the1,6-methano[10]annulenno [3,4-g]-anthraquinone derivatives can act as the promising cathode materials in the lithium battery.This paper also discussed the synthesis of1,6-di(β-ethyl acrylate)-1,3,5-cycloheptatriene, which was prepared from1,3,5-cycloheptatriene-1,6-dialdehyde. The target product was characterized by IR, NMR spectra. We obtained the single crystal of the compound by a method of slowly-solution-cooling. X-ray single crystal diffraction experiments was used to determine crystal structural data.