以2-(2-硝基苯氧基)-1-溴乙烷或3-(2-硝基苯氧基)-1-溴丙烷为原料分别在氢化钠作用下与N-Boc-4-羟基哌啶反应,得到了与预期结构不同的产物.该产物的结构经1H NMR,13C NMR,LC-MS分析表明,其并非为原料2-(2-硝基苯氧基)-1-溴乙烷与N-Boc-4-羟基哌啶发生Williamson反应生成预期的混合醚,而是芳环上的烷氧基被取代的异常产物.根据这个实验结果,推测上述反应的可能机理是发生了芳环上的亲核取代反应.
The unexpected product from reaction of 2-(2-nitrophenoxy)-1-bromoethane or 3-(2-nitro-phenoxy)-1-bromopropane with N-Boc-4-hydroxypiperidine was obtained and the data of 1H NMR,13C NMR and LC-MS of the product indicated that no Williamson reaction happened,instead,the alkyloxy in alkyloxy-nitrobenzene was substituted by N-Boc-4-hydroxypiperidine.Based on the fact,possible mechanism of the reaction was discussed.