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Diastereospecific and Highly Site-Selective Functionalization of C-70 Fullerene by a Reaction with Diethyl N-Arylaziridine-2,3-dicarboxylates. / Lukyanov, Daniil A.; Konev, Alexander S.; Amsharov, Konstantin; Khlebnikov, Alexander F.; Hirsch, Andreas.

In: Journal of Organic Chemistry, Vol. 83, No. 22, 16.11.2018, p. 14146-14151.

Research output: Contribution to journal › Article › peer-review

Harvard

Lukyanov, DA, Konev, AS, Amsharov, K, Khlebnikov, AF & 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, vol. 83, no. 22, pp. 14146-14151. https://doi.org/10.1021/acs.joc.8b02240

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

Vancouver

Lukyanov DA, Konev AS, Amsharov K, Khlebnikov AF, Hirsch A. Diastereospecific and Highly Site-Selective Functionalization of C-70 Fullerene by a Reaction with Diethyl N-Arylaziridine-2,3-dicarboxylates. Journal of Organic Chemistry. 2018 Nov 16;83(22):14146-14151. https://doi.org/10.1021/acs.joc.8b02240

Author

Lukyanov, Daniil A. ; Konev, Alexander S. ; Amsharov, Konstantin ; Khlebnikov, Alexander F. ; Hirsch, Andreas. / Diastereospecific and Highly Site-Selective Functionalization of C-70 Fullerene by a Reaction with Diethyl N-Arylaziridine-2,3-dicarboxylates. In: Journal of Organic Chemistry. 2018 ; Vol. 83, No. 22. pp. 14146-14151.

BibTeX

@article{7746e00485674ec2a63f83fc165dc10f,
title = "Diastereospecific and Highly Site-Selective Functionalization of C-70 Fullerene by a Reaction with Diethyl N-Arylaziridine-2,3-dicarboxylates",
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.",
keywords = "CHARGE SHIFT REACTIONS, 1,3-DIPOLAR CYCLOADDITION, AZOMETHINE YLIDES, STEREOSELECTIVE-SYNTHESIS, ENERGY, SOLVENT, C-60, C-60/C-70, EFFICIENT, DYADS",
author = "Lukyanov, {Daniil A.} and Konev, {Alexander S.} and Konstantin Amsharov and Khlebnikov, {Alexander F.} and Andreas Hirsch",
year = "2018",
month = nov,
day = "16",
doi = "10.1021/acs.joc.8b02240",
language = "Английский",
volume = "83",
pages = "14146--14151",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "22",

}

RIS

TY - JOUR

T1 - Diastereospecific and Highly Site-Selective Functionalization of C-70 Fullerene by a Reaction with Diethyl N-Arylaziridine-2,3-dicarboxylates

AU - Lukyanov, Daniil A.

AU - Konev, Alexander S.

AU - Amsharov, Konstantin

AU - Khlebnikov, Alexander F.

AU - Hirsch, Andreas

PY - 2018/11/16

Y1 - 2018/11/16

N2 - 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.

AB - 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.

KW - CHARGE SHIFT REACTIONS

KW - 1,3-DIPOLAR CYCLOADDITION

KW - AZOMETHINE YLIDES

KW - STEREOSELECTIVE-SYNTHESIS

KW - ENERGY

KW - SOLVENT

KW - C-60

KW - C-60/C-70

KW - EFFICIENT

KW - DYADS

UR - http://www.mendeley.com/research/diastereospecific-highly-siteselective-functionalization-c70-fullerene-reaction-diethyl-narylaziridi

UR - http://www.scopus.com/inward/record.url?scp=85056548850&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b02240

DO - 10.1021/acs.joc.8b02240

M3 - статья

VL - 83

SP - 14146

EP - 14151

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 22

ER -

ID: 36630251