Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, and School of Chemistry and Chemical Engineering, Hubei University , Wuhan 430062, People's Republic of China.
State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, Wuhan Center for Magnetic Resonance, Wuhan Institute of Physics and Mathematics, Chinese Academy of Sciences , Wuhan 430071, People's Republic of China.
J Org Chem. 2017 Sep 15;82(18):9751-9764. doi: 10.1021/acs.joc.7b01968. Epub 2017 Sep 7.
A series of scarce fulleropyrrolines were synthesized via DMAP-mediated one-step reaction of [60]fullerene with commercially inexpensive aromatic aldehydes and arylmethanamines in the absence or presence of manganese(III) acetate. In the case of aminodiphenylmethane, novel 2,5,5-trisubstituted fulleropyrrolines could be easily obtained without the addition of manganese(III) acetate. As for arylmethanamines without α-substitutions, the addition of manganese(III) acetate was required to suppress the formation of fulleropyrrolidines, in order to generate the desired 2,5-disubstituted fulleropyrrolines. Two tautomers were produced as expected when different aryl groups (Ar ≠ Ar) from aromatic aldehydes and arylmethanamines were employed in the synthesis. A plausible reaction mechanism for the formation of fulleropyrrolines is proposed.
通过在不存在或存在醋酸锰的情况下，利用 DMAP 介导的[60]富勒烯与商业上廉价的芳香醛和芳基甲胺的一步反应，合成了一系列罕见的全吡咯啉。对于二苯甲烷胺，在不添加醋酸锰的情况下，很容易得到新型的 2,5,5-三取代全吡咯啉。对于没有α取代的芳基甲胺，需要添加醋酸锰来抑制富勒吡咯啉的形成，以便生成所需的 2,5-二取代富勒吡咯啉。当在合成中使用来自芳香醛和芳基甲胺的不同芳基（Ar ≠ Ar）时，如预期的那样产生了两种互变异构体。提出了一种形成富勒吡咯啉的合理反应机制。
