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Mendeleev Communications, 2016, Volume 26, Issue 6, Pages 535–537
DOI: https://doi.org/10.1016/j.mencom.2016.11.026
(Mi mendc2272)
 

This article is cited in 14 scientific papers (total in 14 papers)

Communications

Synthesis of unsymmetrical N-(2-tert-butylphenyl)-N-(4-tert-butylphenyl)nitroxyl radical, the first stable diarylnitroxyl with vacant para-position

O. A. Levitskiy, V. V. Sentyurin, A. V. Bogdanov, T. V. Magdesieva

Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
Abstract: The title compound, first example of a stable diarylnitroxyl with vacant para-position, was best synthesized by CuCl-assisted coupling of o-tert-butylnitrosobenzene and p-tert-butylphenylboronic acid followed by N-xidation of the thus obtained unsymmetrical diarylamine. ESR investigation showed that ortho-substituted aromatic ring is removed from the conjugation plane providing unusual stability of this radical.
Document Type: Article
Language: English


Citation: O. A. Levitskiy, V. V. Sentyurin, A. V. Bogdanov, T. V. Magdesieva, “Synthesis of unsymmetrical N-(2-tert-butylphenyl)-N-(4-tert-butylphenyl)nitroxyl radical, the first stable diarylnitroxyl with vacant para-position”, Mendeleev Commun., 26:6 (2016), 535–537
Linking options:
  • https://www.mathnet.ru/eng/mendc2272
  • https://www.mathnet.ru/eng/mendc/v26/i6/p535
  • This publication is cited in the following 14 articles:
    1. Oleg A Levitskiy, Yuri K Grishin, Tatiana V Magdesieva, “Novel oxidative routes to N-arylpyridoindazolium salts”, Beilstein J. Org. Chem., 20 (2024), 1906  crossref
    2. Oleg A. Levitskiy, Alexey V. Bogdanov, Ivan A. Klimchuk, Tatiana V. Magdesieva, “Pyridine‐Containing Donor‐Acceptor Diarylnitroxides: Noncovalent Stabilization of the Redox States”, ChemPlusChem, 87:3 (2022)  crossref
    3. E. V. Tretyakov, V. I. Ovcharenko, A. O. Terent'ev, I. B. Krylov, T. V. Magdesieva, D. G. Mazhukin, N. P. Gritsan, “Conjugated nitroxides”, Russian Chem. Reviews, 91:2 (2022), RCR5025  mathnet  mathnet  crossref  isi  scopus
    4. Oleg A. Levitskiy, Dmitry A. Dulov, Alexey V. Bogdanov, Yury K. Grishin, Sergey E. Nefedov, Tatiana V. Magdesieva, “Chameleonic Behavior of the α‐Methylcyclopropyl Group and Its Through‐Space Interactions: A Route to Stabilized Three Redox States in Diarylnitroxides”, Chemistry A European J, 26:30 (2020), 6793  crossref
    5. Vyacheslav V. Sentyurin, Oleg A. Levitskiy, Tatiana V. Magdesieva, “Molecular design of ambipolar redox-active open-shell molecules: Principles and implementations”, Current Opinion in Electrochemistry, 24 (2020), 15  crossref
    6. Oleg A. Levitskiy, Dmitry A. Dulov, Alexey V. Bogdanov, Tatiana V. Magdesieva, “Carbon‐ and SO2‐Locked Diarylnitroxides: Quantum Chemical Consideration, Synthesis, and Electrochemistry”, Eur J Org Chem, 2019:36 (2019), 6225  crossref
    7. Silvia Roscales, Aurelio G. Csákÿ, “Synthesis of Mono-N-Methyl Aromatic Amines from Nitroso Compounds and Methylboronic Acid”, ACS Omega, 4:9 (2019), 13943  crossref
    8. Subhra Kanti Roy, Anuj Tiwari, Mohammed Saleem, Chandan K. Jana, “Metal free direct C(sp2)–H arylaminations using nitrosoarenes to 2-hydroxy-di(het)aryl amines as multifunctional Aβ-aggregation modulators”, Chem. Commun., 54:100 (2018), 14081  crossref
    9. Oleg A. Levitskiy, Vyacheslav V. Sentyurin, Tatiana V. Magdesieva, “Twisting of diarylnitroxides: An efficient tool for redox tuning”, Electrochimica Acta, 260 (2018), 459  crossref
    10. Alexey Bogdanov, Oleg Levitskiy, Andrey Vorobiev, Tatiana Magdesieva, “Stability of twisted diarylnitroxides: Photochemical tests”, Tetrahedron Letters, 59:32 (2018), 3124  crossref
    11. Silvia Roscales, Aurelio G. Csákÿ, “Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling”, Org. Lett., 20:6 (2018), 1667  crossref
    12. O. A. Levitskiy, T. V. Magdesieva, “Computational electrochemistry of diarylnitroxides”, Mendeleev Commun., 28:2 (2018), 187–189  mathnet  crossref
    13. T. V. Magdesieva, O. A. Levitskiy, “Molecular design of stable diarylnitroxides”, Russian Chem. Reviews, 87:7 (2018), 707–725  mathnet  mathnet  crossref  isi  scopus
    14. Nils Jürgensen, Andreas Kretzschmar, Stefan Höfle, Jan Freudenberg, Uwe H. F. Bunz, Gerardo Hernandez-Sosa, “Sulfone-Based Deep Blue Thermally Activated Delayed Fluorescence Emitters: Solution-Processed Organic Light-Emitting Diodes with High Efficiency and Brightness”, Chem. Mater., 29:21 (2017), 9154  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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