Diastereospecific and Highly Site-Selective Functionalization of C-70 Fullerene by a Reaction with Diethyl N-Arylaziridine-2,3-dicarboxylates
Lukyanov DA, Konev AS, Amsharov K, Khlebnikov AF, Hirsch A (2018)
Publication Status: Published
Publication Type: Journal article, Original article
Publication year: 2018
Journal
Publisher: AMER CHEMICAL SOC
Book Volume: 83
Pages Range: 14146-14151
Journal Issue: 22
Abstract
The diastereospecific and highly site-selective cycloaddition of N-arylazomethine ylides generated in situ from diethyl N-arylaziridine-2,3-dicarboxylates to C-70 fullerene is reported. The reaction provides C-70 fulleropyrrolidines in up to hundreds on a milligram scale as alpha- and beta-adducts in a 4:1 ratio with a controlled stereochemical outcome: cis-aziridines give exclusively trans-adducts, and trans-aziridines give only cis-adducts. The H-1 and C-13{H-1} NMR spectra for different isomeric adducts were recorded and analyzed to identify some characteristic features, which permit an easy identification of isomeric adducts of this type.
Authors with CRIS profile
Konstantin Amsharov
Naturwissenschaftliche Fakultät
Andreas Hirsch
Lehrstuhl für Organische Chemie II
Involved external institutions
Russian Federation (RU)How to cite
APA:
Lukyanov, D.A., Konev, A.S., Amsharov, K., Khlebnikov, A.F., & Hirsch, A. (2018). Diastereospecific and Highly Site-Selective Functionalization of C-70 Fullerene by a Reaction with Diethyl N-Arylaziridine-2,3-dicarboxylates. Journal of Organic Chemistry, 83(22), 14146-14151. https://doi.org/10.1021/acs.joc.8b02240
MLA:
Lukyanov, Daniil A., et al. "Diastereospecific and Highly Site-Selective Functionalization of C-70 Fullerene by a Reaction with Diethyl N-Arylaziridine-2,3-dicarboxylates." Journal of Organic Chemistry 83.22 (2018): 14146-14151.
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