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Functionalization of sterically hindered catechol and o-benzoquinone with 2,2,6,6-tetramethylpiperidine 1-oxyl

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Abstract

Sterically hindered 4,6-di-tert-butyl-3-formylcatechol and 3,6-di-tert-butyl-o-benzoquinone react with 4-amino-2,2,6,6-tetramethylpiperidine 1-oxyl to give new chelate ligands of the o-quinone type bearing a 2,2,6,6-tetramethylpiperidine 1-oxyl neutral radical moiety. Structures of the synthesized compounds were established by ESR spectroscopy, IR spectroscopy, mass spectrometry, and X-ray diffraction analysis.

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References

  1. C. G. Pierpont, R. M. Buchanan, Coord. Chem. Rev., 1981, 38, 45.

    Article  CAS  Google Scholar 

  2. C. G. Pierpont, C. W. Lange, Prog., Inorg. Chem., 1994, 41, 331.

    CAS  Google Scholar 

  3. C. G. Pierpont, Coord. Chem. Rev., 2001, 219–221, 415.

    Article  Google Scholar 

  4. V. I. Ovcharenko, E. V. Gorelik, S. V. Fokin, G. V. Romanenko, V. N. Ikorskii, A. V. Krashilina, V. K. Cherkasov, G. A. Abakumov, J. Am. Chem. Soc., 2007, 129, 10512.

    Article  CAS  Google Scholar 

  5. E. Yu. Fursova, O. V. Kuznetsova, E. V. Tretyakov, G. V. Romanenko, A. S. Bogomyakov, V. I. Ovcharenko, R. Z. Sagdeev, V. K. Cherkasov, M. P. Bubnov, G. A. Abakumov, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 809 [Izv. Akad. Nauk, Ser. Khim., 2011, 791].

    Article  CAS  Google Scholar 

  6. A. Yamaguchi, K. Awaga, J. Mater. Chem., 2001, 11, 2142.

    Article  CAS  Google Scholar 

  7. (a)_D. A. Shultz, S. H. Bodnar, K. E. Vostrikova, J. W. Kampf, Inorg. Chem., 2000, 39, 6091

    Article  CAS  Google Scholar 

  8. E. Depperman, S. H. Bodnar, K. E. Vostrikova, D. A. Shultz, M.L. Kirk, J. Am. Chem. Soc., 2001, 123, 3133

    Article  CAS  Google Scholar 

  9. D. Shultz, K Vostrikova, S. Bodnar, H. Koo, M. Whangbo, M. Kirk, E. Depperman, J. Kampf, J. Am. Chem. Soc., 2003, 125, 1607

    Article  CAS  Google Scholar 

  10. M. L. Kirk, D. A. Shultz, E. C. Depperman, Polyhedron, 2005, 24, 2880

    Article  CAS  Google Scholar 

  11. D. A. Shultz, R. K. Kumar, S. Bin-Salamon, M. L. Kirk, Polyhedron, 2005, 24, 2876

    Article  CAS  Google Scholar 

  12. D. E. Stasiw, J. Zhang, G. Wang, R. Dangi, B. W. Stein, D. A. Shultz, M. L. Kirk, L. Wojtas, R. D. Sommer, J. Am. Chem. Soc., 2015, 137, 9222.

    Article  CAS  Google Scholar 

  13. G. A. Abakumov, V. I. Nevodchikov, N. V. Zaitova, N. O. Druzhkov, L. G. Abakumova, Yu. A. Kurskii, V. K. Cherkasov, Russ. Chem. Bull. (Engl. Transl.), 1997, 46, 2093 [Izv. Akad. Nauk, Ser. Khim., 1997, 2206]

    Article  CAS  Google Scholar 

  14. G. A. Abakumov, V. I. Nevodchikov, N. V. Zaitova, N. O. Druzhkov, L. G. Abakumova, Yu. A. Kurskii, V. K. Cherkasov, Russ. Chem. Bull. (Engl. Transl.), 1997, 46, 337 [Izv. Akad. Nauk, Ser. Khim., 1997, 351].

    Article  CAS  Google Scholar 

  15. G. A. Abakumov, V. K. Cherkasov, L. G. Abakumova, N. O. Druzhkov, V. I. Nevodchikov, Yu. A. Kurskii, N. P. Makarenko, Metalloorg. Khim., 1991, 925 [Organomet. Chem. USSR (Engl. Transl.), 1991]

    Google Scholar 

  16. G. A. Abakumov, V. K. Cherkasov, L. G. Abakumova, V. I. Nevodchikov, N. O. Druzhkov, N. P. Makarenko, Yu. A. Kursky, J. Organometallic Chem., 1995, 491, 127.

    Article  CAS  Google Scholar 

  17. M. P. Shurygina, N. O. Druzhkov, M. V. Arsen’ev, M. P. Bubnov, G. K. Fukin, S. A. Chesnokov, V. K. Cherkasov, Russ. J. Org. Chem. (Engl. Transl.), 2011, 47, 486 [Zh. Org. Khim., 2011, 47, 490].

    Article  CAS  Google Scholar 

  18. G. A. Abakumov, V. K. Cherkasov, T. N. Kocherova, N. O. Druzhkov, Yu. A. Kurskii, L. G. Abakumova, Russ. Chem. Bull. (Int. Ed.), 2006, 55, 1195 [Izv. Akad. Nauk, Ser. Khim., 2006, 1151]

    Article  CAS  Google Scholar 

  19. G. A. Abakumov, V. K. Cherkasov, T. N. Kocherova, N. O. Druzhkov, Yu. A. Kurskii, M. P. Bubnov, G. K. Fukin, L. G. Abakumova, Russ. Chem. Bull. (Int Ed.), 2007, 56, 1849 [Izv. Akad. Nauk, Ser. Khim., 2007, 1786].

    Article  CAS  Google Scholar 

  20. M. V. Arsenyev, E. V. Baranov, S. A. Chesnokov, G. Abakumov, Acta Crystallogr. Sect. E: Struct. Rep. Online, 2013, 69, o1565.

    Article  CAS  Google Scholar 

  21. M. V. Arsenyev, PhD Thes. (Chem.), G. A. Razuvaev Institute of Organometallic Chemistry of RAS, Nizhni Novgorod, 2014, 142 pp. (in Russian).

    Google Scholar 

  22. (a)_M. V. Arsenyev, E. V. Baranov, S. A. Chesnokov, V. K. Cherkasov, G. A. Abakumov, Russ. Chem. Bull. (Int. Ed.), 2013, 62, 2394 [Izv. Akad. Nauk, Ser. Khim., 2013, 2394]

    Article  CAS  Google Scholar 

  23. M. V. Arsenyev, N. M. Khamaletdinova, E. V. Baranov, S. A. Chesnokov, V. K. Cherkasov, Russ. Chem. Bull. (Int. Ed.), 2016, 65, 1805 [Izv. Akad. Nauk, Ser. Khim., 2016, 1805]

    Article  CAS  Google Scholar 

  24. M. V. Arsenyev, E. V. Baranov, A. Yu. Fedorov, S. A. Chesnokov, G. A. Abakumov, Mendeleev Commun., 2015, 25, 312.

    Article  CAS  Google Scholar 

  25. V. T. Kasumov, I. Uar, A. Bulut, Y. Yerli, Solid State Sciences, 2011, 13, 1852.

    Article  CAS  Google Scholar 

  26. K. J. Winstanley, D. K. Smith, J. Org. Chem., 2007, 72, 2803.

    Article  CAS  Google Scholar 

  27. H. Pizzala, M. Carles, W. E. E. Stone, A. Thevand, J. Chem. Soc., Perkin Trans., 2000, 2, 935.

    Article  Google Scholar 

  28. S. Nakatsuji, M. Nobusawa, H. Suzuki, H. Akutsu, J. Yamada, J. Org. Chem., 2009, 74, 9345.

    Article  CAS  Google Scholar 

  29. Bruker, APEX2, Bruker Molecular Analysis Research Tool, v. 2013.2-0, Bruker AXS, Madison, Wisconsin, USA, 2013

  30. Bruker, SAINT Data Reduction and Correction Program, v. 8.27B, Bruker AXS, Madison, Wisconsin, USA, 2012

  31. G. M. Sheldrick, SADABS v. 2012/1, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA, 2012

    Google Scholar 

  32. G. M. Sheldrick, SHELXTL v. 6.14, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA, 2003

    Google Scholar 

  33. G. M. Sheldrick, Acta Crystallogr., Sec. A: Found. Adv., 2015, 71, 3.

    Article  Google Scholar 

  34. E. G. Rozantsev, B. D. Sholle, Organic Chemistry of Free Radicals, [Organicheskaya khimiya svobodnikh radikalov], Khimiya, Moscow, 1973, 344 pp. (in Russian).

    Google Scholar 

  35. A. J. Gordon, R. A. Ford, The Chemist’s Companion. A Handbook of Practical Data, Techniques, and References, WileyInterscience, New York,1972.

    Google Scholar 

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Correspondence to V. K. Cherkasov.

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Dedicated to Academician of the Russian Academy of Sciences R. Z. Sagdeev on the occasion of his 75th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2855–2860, December, 2016.

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Druzhkov, N.O., Egorova, E.N., Arsen’ev, M.V. et al. Functionalization of sterically hindered catechol and o-benzoquinone with 2,2,6,6-tetramethylpiperidine 1-oxyl. Russ Chem Bull 65, 2855–2860 (2016). https://doi.org/10.1007/s11172-016-1668-5

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  • DOI: https://doi.org/10.1007/s11172-016-1668-5

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