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含α-活泼氢芳烃与硝基苯的反应及其机理研究
Study on the Reactions and Mechanism of Aromatics Containing Active α-Hydrogen Atom with Nitrobenzene
【摘要】 研究了常温常压下某些芳烃与硝基苯在Lewis酸AlCl3催化作用下的反应,发现含α-活泼氢的芳烃能与硝基苯(PhNO2)反应生成相应的N-苯基芳胺。苊、芴、1-甲基萘(1-MN)、2,6-二甲基萘(2,6-DMN)与PhNO2反应的活性顺序为苊>1-MN>2,6-DMN>芴。由苊与PhNO2的反应,在控制AlCl3与苊的摩尔比为1·2和2·4左右时,重结晶反应产物可得到联苊和5-(N-苯基)氨基苊。根据实验结果,提出苊与PhNO2在AlCl3作用下的反应符合氢阳离子自由基的亲电加成-自由基亲电取代-自由基亲核加成历程。
【Abstract】 At room temperature and ambient atmosphere, the reactions of some aromatics and nitrobenzene catalyzed by AlCl-3 were investigated. The results show that aromatics containing active α-hydrogen atom could react with nitrobenzene to obtain corresponding N-phenyl arylamines. The reaction activity sequence is acenaphthene>1-methyl naphthalene > 2,6 -dimethyl naphthalene >fluorene. Through the reaction of acenaphthene and nitrobenzene, pure biacenaphthenyls and 5-(N-phenyl) aminoacenaphthene were prepared by recrystallizing the reaction mixture obtained under the molar ratio of AlCl-3 to acenaphthene of 1.2 and 2.4, respectively. It can be assumed from the experiments that the reaction pathway of acenaphthene and nitrobenzene with the catalyst of AlCl-3 is the electrophilic addition of cation free radical of hydrogen-free radical electrophilic substitution-free radical nucleophilic addition.
- 【文献出处】 化学通报 ,Chemistry , 编辑部邮箱 ,2006年03期
- 【分类号】O643.12
- 【被引频次】2
- 【下载频次】127