摘要
硫化钠和二硫化钠分别在95%乙醇中与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,13C NMR,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.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2009年第1期105-107,共3页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(No.20676036)资助项目
关键词
2
5-二甲氧基-4-氯硝基苯
硫化钠
硝基还原
亲核取代
2,5-dimethoxy-4-chloronitrobenzene
sodium sulfide
reduction for nitro group
nucleophilic substitution
