硫化钠和二硫化钠分别在95%醇中与2,5-二甲氧基-4-氯硝基苯反应,原本期望得到2,5-二甲氧基-4-氯苯胺,然而对产物结构的^1H NMR,BCNMR,MS以及元素分析结果表明,2,5-二甲氧基-4-氯硝基苯中的硝基没有被硫化钠和二硫化钠还原成氨基,而是其中的氯原子被硫离子(或二硫离子)取代,分别生成了4,4′-硫代-2,2′,5,5′-四甲氧基-双硝基苯和4,4′-双硫代-2,2′,5,5′-四甲氧基双硝基苯.根据这个实验事实,讨论了上述亲核取代反应的机理.
2,5-Dimethoxy-4-chloronitrobenzene reacted with sodium sulfide or sodium disulfide in 95% ethanol, to expect forming 2,5-dimethoxy-4-chloroaniline. However, the data of ^1H NMR, ^13C NMR, MS techniques and elemental analyses of the reaction products indicated that no reduction of nitro group in 2,5-dimethoxy-4-chloronitrobenzene happened, instead, a chlorine atom in 2,5-dimethoxy-4-chloronitro- benzene was replaced by sulfur anion or bis-sulfur anion, affording 4,4′-dinitro-2,2′,5,5′-tetramethoxydi-phenyl-sulfur or 4,4′-dinitro-2,2′,5,5′-tetramethoxy-diphenyl-bis-sulfur, respectively. Based on this fact, a mechanism of the nucleophilic substitution reaction is proposed.