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

DOI: 10.1021/acs.joc.8b02240

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

Involved external institutions

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.

BibTeX: Download