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Shi JL, Li FB, Zhang XF, et al. Synthesis and Functionalization of Symmetrical 2,5-Diaryl Fulleropyrrolidines: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Arylmethanamines. J Org Chem. 2016;81(5):1769-77doi: 10.1021/acs.joc.5b02412.
Shi, J. L., Li, F. B., Zhang, X. F., Wu, J., Zhang, H. Y., Peng, J., Liu, C. X., Liu, L., Wu, P., & Li, J. X. (2016). Synthesis and Functionalization of Symmetrical 2,5-Diaryl Fulleropyrrolidines: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Arylmethanamines. The Journal of organic chemistry, 81(5), 1769-77. https://doi.org/10.1021/acs.joc.5b02412
Shi, Ji-Long, et al. "Synthesis and Functionalization of Symmetrical 2,5-Diaryl Fulleropyrrolidines: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Arylmethanamines." The Journal of organic chemistry vol. 81,5 (2016): 1769-77. doi: https://doi.org/10.1021/acs.joc.5b02412
Shi JL, Li FB, Zhang XF, Wu J, Zhang HY, Peng J, Liu CX, Liu L, Wu P, Li JX. Synthesis and Functionalization of Symmetrical 2,5-Diaryl Fulleropyrrolidines: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Arylmethanamines. J Org Chem. 2016 Mar 04;81(5):1769-77. doi: 10.1021/acs.joc.5b02412. Epub 2016 Feb 18. PMID: 26841702.
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J Org Chem. 2016 Mar 04;81(5):1769-77. doi: 10.1021/acs.joc.5b02412. Epub 2016 Feb 18.

Synthesis and Functionalization of Symmetrical 2,5-Diaryl Fulleropyrrolidines: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Arylmethanamines.

The Journal of organic chemistry

Ji-Long Shi, Fa-Bao Li, Xiao-Feng Zhang, Jun Wu, Hong-Yu Zhang, Jie Peng, Chun-Xiang Liu, Li Liu, Ping Wu, Jia-Xing Li

Affiliations

  1. 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.
  2. College of Chemistry and Chemical Engineering, Key Laboratory of Coordination Chemistry and Functional Materials in Universities of Shandong, Dezhou University , Dezhou 253023, People's Republic of China.
  3. Key Laboratory of Novel Thin Film Solar Cells, Institute of Plasma Physics, Chinese Academy of Sciences , P.O. Box 1126, Hefei 230031, People's Republic of China.

PMID: 26841702 DOI: 10.1021/acs.joc.5b02412

Abstract

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.

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