Synthesis and Functionalization of Symmetrical 2,5-Diaryl Fulleropyrrolidines: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Arylmethanamines
| Autor: | Ji-Long Shi, Chun-Xiang Liu, Jiaxing Li, Hong-Yu Zhang, Li Liu, Fa-Bao Li, Jie Peng, Jun Wu, Ping Wu, Xiao-Feng Zhang |
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| Rok vydání: | 2016 |
| Předmět: |
Fullerene
010405 organic chemistry Chemistry Organic Chemistry One-Step 010402 general chemistry Photochemistry 01 natural sciences Chloride Medicinal chemistry Isocyanate Ferric perchlorate 0104 chemical sciences chemistry.chemical_compound medicine Surface modification Stereoselectivity Cis–trans isomerism medicine.drug |
| Zdroj: | The Journal of Organic Chemistry. 81:1769-1777 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.5b02412 |
| Popis: | A series of scarce N-unsubstituted 2,5-diaryl fulleropyrrolidines as cis isomers could be prepared via the facile one-step reaction of [60]fullerene with N-unsubstituted arylmethanamines promoted by cheap and easily available ferric perchlorate. Nevertheless, the reaction of N-substituted arylmethanamines with [60]fullerene under the same conditions gave different experimental results. N-Methylbenzylamine formed N-methyl 2,5-diphenyl fulleropyrrolidine as a trans isomer, and N,N-dibenzylamine unexpectedly afforded the N-unsubstituted 2,5-diphenyl fulleropyrrolidine as a cis isomer. Intriguingly, high stereoselectivity for all 2,5-diaryl fulleropyrrolidines could be observed although both cis and trans isomers were possibly formed. N-Unsubstituted fulleropyrrolidine could be further converted to N-substituted fulleropyrrolidines under the assistance of an acid chloride or an isocyanate. A possible reaction pathway leading to 2,5-diaryl fulleropyrrolidines is also proposed. |
| Databáze: | OpenAIRE |
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