Synthesis of unsymmetrical N-(2-tert-butylphenyl)-N-(4-tert-butylphenyl)nitroxyl radical, the first stable diarylnitroxyl with vacant para-position
[Display omitted] 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 investi...
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Published in | Mendeleev communications Vol. 26; no. 6; pp. 535 - 537 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
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Elsevier B.V
01.11.2016
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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. |
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AbstractList | [Display omitted]
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. |
Author | Magdesieva, Tatiana V. Bogdanov, Alexey V. Levitskiy, Oleg A. Sentyurin, Vyacheslav V. |
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References | Ley, Thomas (bib0065) 2003; 42 Rajca, Shiraishi, Rajca (bib0055) 2009 Surry, Buchwald (bib0010) 2011; 2 Denisov (bib0005) 1996; 65 Oka, Kouno, Tanaka (bib0050) 2007; 17 Ballester, Riera, Onrubia (bib0030) 1976; 17 Golubev, Sen (bib0060) 2013; 49 Delen, Lahti (bib0045) 2006; 71 Lalic, Rucker (bib0015) 2013; 24 Correa, Carril, Bolm (bib0020) 2008; 14 Shekhar, Shen, Barrios-Landeros, Hartwig (bib0025) 2007 Tsedilin, Fakhrutdinov, Eremin, Zalesskiy, Chizhov, Kolotyrkina, Ananikov (bib0080) 2015; 25 Ishida, Iwamura (bib0035) 1991; 113 Tanaka, Matsuda, Itoh, Iwamura (bib0040) 1998; 120 Qiao, Lam (bib0075) 2011 Vantourout, Law, Isidro-Llobet, Atkinson, Watson (bib0070) 2016; 4 Ishida (10.1016/j.mencom.2016.11.026_bib0035) 1991; 113 Golubev (10.1016/j.mencom.2016.11.026_bib0060) 2013; 49 Vantourout (10.1016/j.mencom.2016.11.026_bib0070) 2016; 4 Surry (10.1016/j.mencom.2016.11.026_bib0010) 2011; 2 Ley (10.1016/j.mencom.2016.11.026_bib0065) 2003; 42 Ballester (10.1016/j.mencom.2016.11.026_bib0030) 1976; 17 Tsedilin (10.1016/j.mencom.2016.11.026_bib0080) 2015; 25 Denisov (10.1016/j.mencom.2016.11.026_bib0005) 1996; 65 Shekhar (10.1016/j.mencom.2016.11.026_bib0025) 2007 Delen (10.1016/j.mencom.2016.11.026_bib0045) 2006; 71 Oka (10.1016/j.mencom.2016.11.026_bib0050) 2007; 17 Correa (10.1016/j.mencom.2016.11.026_bib0020) 2008; 14 Tanaka (10.1016/j.mencom.2016.11.026_bib0040) 1998; 120 Rajca (10.1016/j.mencom.2016.11.026_bib0055) 2009 Qiao (10.1016/j.mencom.2016.11.026_bib0075) 2011 Lalic (10.1016/j.mencom.2016.11.026_bib0015) 2013; 24 |
References_xml | – volume: 17 start-page: 1209 year: 2007 ident: bib0050 publication-title: J. Mater. Chem. – volume: 14 start-page: 10919 year: 2008 ident: bib0020 publication-title: Chem. Eur. J. – volume: 65 start-page: 505 year: 1996 ident: bib0005 publication-title: Russ. Chem. Rev. – volume: 2 start-page: 27 year: 2011 ident: bib0010 publication-title: Chem. Sci. – volume: 42 start-page: 5400 year: 2003 ident: bib0065 publication-title: Angew. Chem. Int. Ed. – volume: 25 start-page: 454 year: 2015 ident: bib0080 publication-title: Mendeleev Commun. – volume: 24 start-page: 269 year: 2013 ident: bib0015 publication-title: Synlett – start-page: 455 year: 2007 end-page: 536 ident: bib0025 publication-title: The Chemistry of Anilines – start-page: 4372 year: 2009 ident: bib0055 publication-title: Chem. Commun. – volume: 120 start-page: 7168 year: 1998 ident: bib0040 publication-title: J. Am. Chem. Soc. – volume: 17 start-page: 945 year: 1976 ident: bib0030 publication-title: Tetrahedron Lett. – volume: 49 start-page: 555 year: 2013 ident: bib0060 publication-title: Russ. J. Org. Chem. – volume: 113 start-page: 4238 year: 1991 ident: bib0035 publication-title: J. Am. Chem. Soc. – volume: 4 start-page: 3942 year: 2016 ident: bib0070 publication-title: J. Org. Chem. – start-page: 829 year: 2011 ident: bib0075 publication-title: Synthesis – volume: 71 start-page: 9341 year: 2006 ident: bib0045 publication-title: J. Org. Chem. – start-page: 829 year: 2011 ident: 10.1016/j.mencom.2016.11.026_bib0075 publication-title: Synthesis doi: 10.1055/s-0030-1258379 – volume: 17 start-page: 945 year: 1976 ident: 10.1016/j.mencom.2016.11.026_bib0030 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)77973-1 – volume: 65 start-page: 505 year: 1996 ident: 10.1016/j.mencom.2016.11.026_bib0005 publication-title: Russ. Chem. Rev. doi: 10.1070/RC1996v065n06ABEH000302 – volume: 14 start-page: 10919 year: 2008 ident: 10.1016/j.mencom.2016.11.026_bib0020 publication-title: Chem. Eur. J. doi: 10.1002/chem.200802018 – volume: 120 start-page: 7168 year: 1998 ident: 10.1016/j.mencom.2016.11.026_bib0040 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja980817g – volume: 4 start-page: 3942 year: 2016 ident: 10.1016/j.mencom.2016.11.026_bib0070 publication-title: J. Org. Chem. doi: 10.1021/acs.joc.6b00466 – volume: 71 start-page: 9341 year: 2006 ident: 10.1016/j.mencom.2016.11.026_bib0045 publication-title: J. Org. Chem. doi: 10.1021/jo0616299 – volume: 2 start-page: 27 year: 2011 ident: 10.1016/j.mencom.2016.11.026_bib0010 publication-title: Chem. Sci. doi: 10.1039/C0SC00331J – start-page: 4372 year: 2009 ident: 10.1016/j.mencom.2016.11.026_bib0055 publication-title: Chem. Commun. doi: 10.1039/b909741d – volume: 49 start-page: 555 year: 2013 ident: 10.1016/j.mencom.2016.11.026_bib0060 publication-title: Russ. J. Org. Chem. doi: 10.1134/S1070428013040106 – volume: 25 start-page: 454 year: 2015 ident: 10.1016/j.mencom.2016.11.026_bib0080 publication-title: Mendeleev Commun. doi: 10.1016/j.mencom.2015.11.019 – volume: 42 start-page: 5400 year: 2003 ident: 10.1016/j.mencom.2016.11.026_bib0065 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.200300594 – volume: 113 start-page: 4238 year: 1991 ident: 10.1016/j.mencom.2016.11.026_bib0035 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00011a028 – volume: 24 start-page: 269 year: 2013 ident: 10.1016/j.mencom.2016.11.026_bib0015 publication-title: Synlett doi: 10.1055/s-0032-1317744 – start-page: 455 year: 2007 ident: 10.1016/j.mencom.2016.11.026_bib0025 – volume: 17 start-page: 1209 year: 2007 ident: 10.1016/j.mencom.2016.11.026_bib0050 publication-title: J. Mater. Chem. doi: 10.1039/B610365K |
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Title | Synthesis of unsymmetrical N-(2-tert-butylphenyl)-N-(4-tert-butylphenyl)nitroxyl radical, the first stable diarylnitroxyl with vacant para-position |
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