【作者】 李明明；

【导师】 葛春华；

【作者基本信息】 辽宁大学 ， 有机化学， 2011， 硕士

【摘要】 二茂铁是一种具有芳香性的有机过渡金属化合物,自被发现以来,以其新奇的分子结构及其突出的芳香性引起了众多金属有机化学研究者的强烈兴趣。本文主要合成的是N-[4-(二茂铁基)]苯基酰胺类化合物。从原料4-硝基苯胺出发,通过重氮化反应与二茂铁反应生成4-二茂铁基硝基苯;再通过硝基还原氨基反应,把4-二茂铁基硝基苯还原成4-二茂铁基苯胺。以11种羧酸与氯化亚砜反应生成酰氯,再与已合成的4-二茂铁基苯胺发生酰胺反应,生成11种N-[4-(二茂铁基)]苯基酰胺类化合物,具体为:N-[4-(二茂铁基)]苯基-3-吡啶甲酰胺、N-[4-(二茂铁基)苯基]-4-吡啶甲酰胺、N-[4-(二茂铁基)苯基]苯甲酰胺、N-[4-(二茂铁基)苯基]-3,5-二硝基苯甲酰胺、N-[4-(二茂铁基)苯基]-3-苯基丙烯酰胺、N-[4-(二茂铁基)苯基]-4-氯苯甲酰胺、N-[4-(二茂铁基)苯基]-3-氯苯甲酰胺、N-[4-(二茂铁基)苯基]-2-氯苯甲酰胺、N-[4-(二茂铁基)苯基]-4-硝基苯甲酰胺、N-[4-(二茂铁基)苯基]-3-硝基苯甲酰胺、N-[4-(二茂铁基)苯基]-2-硝基苯甲酰胺。以上13种化合物均经过红外、核磁等表征,部分化合物通过了质谱的验证,确定了结构。本论文合成表征的13种化合物中,有10种是SciFinder没有收录的,分别是:N-[4-(二茂铁基)]苯基-3-吡啶甲酰胺、N-[4-(二茂铁基)苯基]-4-吡啶甲酰胺、N-[4-(二茂铁基)苯基]-3,5-二硝基苯甲酰胺、N-[4-(二茂铁基)苯基]-3-苯基丙烯酰胺、N-[4-(二茂铁基)苯基]-4-氯苯甲酰胺、N-[4-(二茂铁基)苯基]-3-氯苯甲酰胺、N-[4-(二茂铁基)苯基]-2-氯苯甲酰胺、N-[4-(二茂铁基)苯基]-4-硝基苯甲酰胺、N-[4-(二茂铁基)苯基]-3-硝基苯甲酰胺、N-[4-(二茂铁基)苯基]-2-硝基苯甲酰胺。更多还原

【Abstract】 Ferrocene is a kind of aromatic organic transition-metal complexes.As its novel structure and outstanding aromaticity, ferrocene attracts strong interests of researchers in organometallic chemistry since it was found.N-[4-(ferrocenyl)phenyl] amides were synthesized in this thesis. First 4-ferrocenyl nitrobenzene was synthesized using 4-nitroaniline and ferrocene through diazotization reaction. And then 4-ferrocenyl nitrobenzene was deoxidized to 4-ferrocenylaniline. Eleven carboxylic acids were reacted with sulfoxide chloride, and thionyl chlorides were got. Then they were reacted with the synthesized 4-ferrocenylanilines through aniline reaction making eleven N-[4-(ferrocenyl) phenyl] amides. As follows:N-[4-(ferrocenyl) phenyl]-3-pyridyl carboxamide, N-[4-(ferrocenyl) phenyl]-4-pyridyl carboxamide, N-[4-(ferrocenyl) phenyl] benzamide, N-[4-(ferrocenyl) phenyl]-3,5-dinitrobenzamide, N-[4-(ferrocenyl) phenyl]-3-phenyl acrylamide, N-[4-(ferrocenyl) phenyl]-4-chlorobenzamide, N-[4-(ferrocenyl) phenyl]-3- chlorobenzamide, N-[4-(ferrocenyl) phenyl]-2-chlorobenzamide, N-[4-(ferrocenyl) phenyl]-4-nitrobenzamide, N-[4-(ferrocenyl) phenyl]-3-nitrobenzamide, N-[4-(ferrocenyl) phenyl]-2-nitrobenzamide.All the compounds synthesized in this thesis have been verified by IR and 1H NMR.Some ones have been tested by MS.Ten compounds synthesized and characterized in this thesis are not included in SciFinder, and they are as follows: N-[4-(ferrocenyl) phenyl]-3-pyridyl carboxamide, N-[4-(ferrocenyl) phenyl]-4-pyridyl carboxamide, N-[4-(ferrocenyl) phenyl]-3,5-dinitrobenzamide, N-[4-(ferrocenyl) phenyl]-3-phenyl acrylamide, N-[4-(ferrocenyl) phenyl]-4-chlorobenzamide, N-[4-(ferrocenyl) phenyl]-3- chlorobenzamide, N-[4-(ferrocenyl) phenyl]-2-chlorobenzamide, N-[4-(ferrocenyl) phenyl]-4-nitrobenzamide, N-[4-(ferrocenyl) phenyl]-3-nitrobenzamide, N-[4-(ferrocenyl) phenyl]-2-nitrobenzamide.更多还原