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本文报道全氟苯、一氯五氟苯和二氯四氟苯与仲胺在DMF或HMPA中的亲核反应结果。C_6F_5Cl与仲胺反应生成对位产物。C_6F_4Cl_2(m:o:p=73:18:9)与仲胺的反应,只有m-和o-异构体能生成预期产物,而p-C_6F_4Cl_2只与活性高的四氢吡咯反应。延长反应时间和提高反应温度,C_6F_6可给出对位双取代产物。六个仲胺的反应活性顺序是:四氢吡咯>哌啶>吗啡啉>二乙胺>二正丙胺>二异丙胺。
This article reports the results of the nucleophilic reaction of perfluorobenzene, chloropentafluorobenzene and dichlorotetrafluorobenzene with secondary amines in DMF or HMPA. C_6F_5Cl reacts with the secondary amine to produce the para-product. The reaction of C_6F_4Cl_2 (m: o: p = 73: 18: 9) with secondary amine showed that only the m- and o-isomers produced the expected product, while p-C_6F_4Cl_2 only reacted with the highly active tetrahydropyrrole. Extend the reaction time and increase the reaction temperature, C_6F_6 can give the para disubstituted products. The reactivity of the six secondary amines was: pyrrolidine> piperidine> morpholine> diethylamine> di-n-propylamine> diisopropylamine.