用GC/MS研究含α-活泼氢芳烃与硝基苯的反应

在常温常压下，研究了苊、蒽、萘、芴、1-甲基萘（1-MN）、2,6-二甲基萘（2,6-DMN）、苯酚、α-萘酚与PhNO2(硝基苯)在Lewis酸AlCl3催化作用下的反应。结果发现，蒽、萘和苯酚与PhNO2不反应，苊、芴、1-MN、2,6-DMN和α-萘酚与PhNO2都能反应生成相应的苯胺基芳烃。GC/MS分析表明反应活性顺序为苊＞1-MN＞2,6-DMN＞芴，根据超共轭效应可以合理解释含α-活泼氢芳烃反应活性顺序。控制AlCl3与苊的摩尔比值为1.2和2.4左右，重结晶苊与PhNO2的反应产物分别得到联苊和5-苯胺基苊纯品，利用GC、GC/MS、FTIR和UV等分析测试手段对其进行了结构鉴定。

STUDY ON THE REACTION OF AROMATICS CONTAINING ACTIVE α-HYDROGEN ATOM WITH NITROBENZENE BY GC/MS

At room temperature and ambient atmosphere, the reactions of acenaphthene, anthracene, naphthalene, fluorine, 1-methylnaphthalene, 2,6-dimethylnaphthalene, phenol and α-naphthol with nitrobenzene over the high active catalyst of AlCl3 were investigated. The results show anthracene, naphthalene and phenol do not react with PhNO2, while acenaphthene, fluorine, 1-methylnaphthalene, 2,6-dimethylnaphthalene and α-naphthol could react with PhNO2 to give corresponding anilinoaromatics. The reaction activity sequence of acenaphthene > 1-MN > 2,6-DMN>fluorine, which deduced by GC/MS analysis, is reasonably explained according to ultra-conjugate effect. The reaction of acenaphthene and PhNO2 is carried out under different conditions, in which the molar ratio of AlCl3 to acenaphthene is 1.2 and 2.4, respectively. Pure biacenaphthenyls and 5-anilinoacenaphthene are prepared by recrystalling the reaction product. The structures of these compounds are identified by GC, GC/MS，FTIR and UV analyses.