In this work, the model reaction of benzaldehyde and ammonium chloride has been studied by detailed product analysis and characterization. Subsequently, amarine and iso-amarine hydrochlorides (, ), dimethylated amarine and iso-amarine ionic salts (, ), together with monomethylated Tröger's-base ionic salt () have been separately synthesized and characterized. In addition, their catalytic performance towards the cycloaddition of CO to epichlorohydrin is compared under identical conditions. It is observed that their catalytic activity follows the order of ≈ > > ≈ . Inspired by the highly catalytic activity of , and , a novel monomethylated Tröger's-base-containing polyimidazolinium salt (namely PMDD-IL) has been synthesized by one-pot reaction of Tröger's-base-containing dialdehyde monomer (MDD) with ammonium chloride followed by treatment with excess iodomethane in the presence of sodium hydride. The as-synthesized PMDD-IL network exhibits highly catalytic activity towards the cycloaddition of CO to epoxides, providing nearly quantitative selectivity (99%) and conversion (99%) over a wide substrate scope of epoxides at atmospheric CO pressure (epichlorohydrin, 100 °C/10 h; epibromohydrin, 100 °C/12 h; glycidyl phenyl ether, 100 °C/24 h; styrene oxide, 100 °C/24 h; and 2-butyloxirane, 100 °C/24 h). The excellent catalytic activity of PMDD-IL network can be ascribed to the high nucleophilicity of iodine anion along with the strong interactions between PMDD-IL network and CO molecules.

中文翻译：

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含单甲基化特罗格碱的聚咪唑啉鎓盐作为 CO2 环加成的有效催化剂

在这项工作中，通过详细的产物分析和表征，研究了苯甲醛和氯化铵的模型反应。随后，分别合成并表征了青青和异青青盐酸盐 (, )、二甲基化青青和异青青离子盐 (, ) 以及单甲基化特罗格碱离子盐 () 。此外，在相同条件下比较了它们对 CO 与环氧氯丙烷环加成的催化性能。据观察，它们的催化活性遵循 ≈ > > ≈ 的顺序。受 、 和 的高催化活性的启发，通过含 Tröger's 碱的二醛单体（MDD）与氯化铵的一锅反应合成了一种新型单甲基化含 Tröger's 碱的聚咪唑啉鎓盐（即 PMDD-IL）。在氢化钠存在下用过量的碘甲烷处理。合成的 PMDD-IL 网络对 CO 与环氧化物的环加成表现出高度催化活性，在大气 CO 压力（环氧氯丙烷，100 ° C/10小时；表溴醇，100℃/12小时；缩水甘油基苯基醚，100℃/24小时；氧化苯乙烯，100℃/24小时；和2-丁基环氧乙烷，100℃/24小时。 PMDD-IL网络优异的催化活性可归因于碘阴离子的高亲核性以及PMDD-IL网络与CO分子之间的强相互作用。