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:
Oleg A Levitskiy, Yuri K Grishin, Tatiana V Magdesieva, “Novel oxidative routes to N-arylpyridoindazolium salts”, Beilstein J. Org. Chem., 20 (2024), 1906
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)
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
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
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
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
Silvia Roscales, Aurelio G. Csákÿ, “Synthesis of Mono-N-Methyl Aromatic Amines from Nitroso Compounds and Methylboronic Acid”, ACS Omega, 4:9 (2019), 13943
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
Oleg A. Levitskiy, Vyacheslav V. Sentyurin, Tatiana V. Magdesieva, “Twisting of diarylnitroxides: An efficient tool for redox tuning”, Electrochimica Acta, 260 (2018), 459
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
O. A. Levitskiy, T. V. Magdesieva, “Computational electrochemistry of diarylnitroxides”, Mendeleev Commun., 28:2 (2018), 187–189
T. V. Magdesieva, O. A. Levitskiy, “Molecular design of stable diarylnitroxides”, Russian Chem. Reviews, 87:7 (2018), 707–725
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