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Isopropyl-substituted o-benzoquinones and oxanthrenequinones. Effect of steric shielding of alkyl substituents on reactivity

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Abstract

A synthetic procedure was developed for the preparation of sterically hindered di- and trisubstituted catechols and o-quinones by the reaction of catechol with isopropanol. Compared to sterically more hindered analogs, o-quinones bearing isopropyl substituents exhibit a higher reactivity toward the formation of oxanthrenequinone derivatives.

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References

  1. C. G. Pierpont, R. M. Buchanan, Coord. Chem. Rev., 1981, 38, 45; DOI: https://doi.org/10.1016/S0010-8545(00)80499-3.

    Article  CAS  Google Scholar 

  2. R. M. Buchanan, C. G. Pierpont, J. Am. Chem. Soc., 1980, 102, 4951; DOI: https://doi.org/10.1021/ja00535a021.

    Article  CAS  Google Scholar 

  3. G. A. Abakumov, V. K. Cherkasov, A. V. Lobanov, Dokl. AN SSSR, 1982, 266, 361 [Dokl. Chem. (Engl. Transl.), 1982, 266].

    CAS  Google Scholar 

  4. G. A. Abakumov, V. I. Nevodchilov, V. K. Cherkasov, Dokl. AN SSSR, 1984, 278, 641 [Dokl. Chem. (Engl. Transl.), 1984, 278].

    CAS  Google Scholar 

  5. G. A. Abakumov, V. I. Nevodchilov, V. K. Cherkasov, Izv. AN SSSR. Ser. Khim., 1986, 35, 54 [Bull. Acad. Sci. USSR. Div. Chem. Sci. (Engl. Transl.), 1986, 35]; DOI: https://doi.org/10.1007/BF00952845.

    Google Scholar 

  6. C. W. Lange, M. Foldeaki, V. I. Nevodchikov, V. K. Cherkasov, G. A. Abakumov, C. G. Pierpont, J. Am. Chem. Soc., 1992, 114, 4220; DOI: https://doi.org/10.1021/ja00037a027.

    Article  CAS  Google Scholar 

  7. A. A. Zolotukhin, M. P. Bubnov, A. V. Arapova, G. K. Fukin, R. V. Rumyantcev, A. S. Bogomyakov, A. V. Knyazev, V. K. Cherkasov, Inorg. Chem., 2017, 56, 14751; DOI: https://doi.org/10.1021/acs.inorgchem.7b02597.

    Article  CAS  Google Scholar 

  8. M. P. Bubnov, N. A. Skorodumova, A. S. Bogomyakov, G. V. Romanenko, A. A. Arapova, K. A. Kozhanov, N. N. Smirnova, G. A. Abakumov, V. K. Cherkasov, Russ. Chem. Bull., 2011, 60, 449; DOI: https://doi.org/10.1007/s11172-011-0071-5.

    Article  CAS  Google Scholar 

  9. G. A. Abakumov, V. I. Nevodchilov, Dokl. AN SSSR, 1982, 266, 1407 [Dokl. Chem. (Engl. Transl.), 1982, 266].

    CAS  Google Scholar 

  10. G. A. Abakumov, V. K. Cherkasov, M. P. Bubnov, O. G. Ellert, Zh. V. Dobrokhotova, L. N. Zakharov, Yu. T. Struchkov, Dokl. AN, 1993, 328, 332 [Dokl. Chem. (Engl. Transl.), 1993, 328]; DOI: https://doi.org/10.1021/acs.inorgchem.0c00547.

    CAS  Google Scholar 

  11. O.-S. Jung, C. G. Pierpont, J. Am. Chem. Soc., 1994, 116, 2229, DOI: https://doi.org/10.1021/ja00084a107.

    Article  CAS  Google Scholar 

  12. M. P. Bubnov, K. A. Kozhanov, N. A. Skorodumova, V. K. Cherkasov, Inorg. Chem., 2020, 59, 6679; DOI: https://doi.org/10.1021/acs.inorgchem.0c00547.

    Article  CAS  Google Scholar 

  13. L. N. Zakharov, Yu. T. Struchkov, G. A. Abakumov, V. I. Nevodchilov, Koord. Khim., 1990, 16, 1101 [J. Coord. Chem. (Engl. Transl.), 1990, 16].

    CAS  Google Scholar 

  14. M. P. Bubnov, V. I. Nevodchikov, G. K. Fukin, V. K. Cherkasov, G. A. Abakumov, Inorg. Chem. Commun., 2007, 10, 989; DOI: https://doi.org/10.1016/j.inoche.2007.05.011.

    Article  CAS  Google Scholar 

  15. M. Mitsumi, S. Umebayashi, Y. Ozawa, M. Tadokoro, H. Kawamura, K. Toriumi, Chem. Lett., 2004, 33, 970; DOI: https://doi.org/10.1246/cl.2004.970.

    Article  CAS  Google Scholar 

  16. M. Mitsumi, H. Goto, S. Umebayashi, Y. Ozawa, M. Kobayashi, T. Yokoyama, H. Tanaka, S.-I. Kuroda, K. A. Toriumi, Angew. Chem., 2005, 44, 4164; DOI: https://doi.org/10.1002/ange.200501189.

    Article  CAS  Google Scholar 

  17. M. Mitsumi, S. Ohtake, Y. Kakuno, Y. Komatsu, Y. Ozawa, K. Toriumi, N. Yasuda, N. Azuma, Y. Miyazaki, Inorg. Chem., 2014, 53, 11710; DOI: https://doi.org/10.1021/ic5019532.

    Article  CAS  Google Scholar 

  18. M. Mitsumi, T. Nishitani, S. Yamasaki, N. Shimada, Y. Komatsu, K. Toriumi, Y. Kitagawa, M. Okumura, Y. Miyazaki, N. Górska, A. Inaba, A. Kanda, N. Hanasaki, J. Am. Chem. Soc., 2014, 136, 7026; DOI: https://doi.org/10.1021/ja5017014.

    Article  CAS  Google Scholar 

  19. R. V. Rumyantcev, G. K. Fukin, G. V. Romanenko, I. A. Teplova, M. P. Bubnov, V. K. Cherkasov, ACS Omega, 2020, 5, 32792; DOI: https://doi.org/10.1021/acsomega.0c05344.

    Article  CAS  Google Scholar 

  20. M. Mitsumi, Y. Komatsu, M. Hashimoto, Y. Kitagawa, Y. Miyazaki, H. Akutsu, H. Akashi, Chem. Eur. J., 2021, 27, 3074; DOI: https://doi.org/10.1002/chem.202004217.

    Article  CAS  Google Scholar 

  21. US Pat. 605483 (2831817).

  22. L. A. Maslovsraya, D. K. Petrikevich, V. A. Timoshchuk, O. I. Shadyro, J. Gen. Chem. (Engl. Transl.), 1996, 66, 1842.

    Google Scholar 

  23. G. A. Abakumov, N. N. Vavilina, Y. A. Kurskii, V. I. Nevodchikov, V. K. Cherkasov, A. S. Shavyrin, Russ. Chem. Bull., 2003, 52, 1847; DOI: https://doi.org/10.1023/A:1026029410312.

    Article  CAS  Google Scholar 

  24. US Pat. 3395160.

  25. T. N. Kocherova, N. O. Druzhkov, K. A. Martyanov, A. S. Shavyrin, M. V. Arsenyev, T. I. Kulikova, E. V. Baranov, V. A. Kuropatov, V. K. Cherkasov, Russ. Chem. Bull., 2020, 69, 2383; DOI: https://doi.org/10.1007/s11172-020-3051-9.

    Article  CAS  Google Scholar 

  26. G. K. Fukin, A. V. Cherkasov, M. P. Shurygina, N. O. Druzhkov, V. A. Kuropatov, S. A. Chesnokov, G. A. Abakumov, Struct. Chem., 2010, 21, 607; DOI: https://doi.org/10.1007/s11224-010-9590-1.

    Article  CAS  Google Scholar 

  27. M. P. Bubnov, V. K. Cherkasov, I. A. Teplova, N. O. Druzhkov, I. D. Grishin, E. V. Baranov, A. S. Bogomyakov, G. A. Abakumov, Dalton Trans., 2019, 48, 10516; DOI: https://doi.org/10.1039/C9DT01309A.

    Article  Google Scholar 

  28. Yu. V. Zefirov, P. M. Zorkiy, Chem. Rev., 1995, 64, 415.

    Google Scholar 

  29. A. René, D. H. Evans, J. Phys. Chem., 2012, 116, 14454; DOI: https://doi.org/10.1021/jp3038335.

    Google Scholar 

  30. G. A. Abakumov, V. K. Cherkasov, L. G. Abakumova, N. O. Druzhkov, V. I. Nevodchikov, Y. A. Kurskii, N. A. Makartnko, Organomet. Chem. USSR, 1991, 4, 454.

    Google Scholar 

  31. M. P. Shurygina, M. Yu. Zakharina, M. A. Baten’kin, A. N. Konev, A. S. Shavyrin, E. A. Chelnokov, N. Yu. Shushunova, M. V. Arsenyev, S. A. Chesnokov, G. A. Abakumov, Eur. Polym. J., 2020, 127, 109573; DOI: https://doi.org/10.1016/j.eurpolymj.2020.109573.

    Article  Google Scholar 

  32. V. A. Palm, Vvedeniye v teoreticheskuyu organicheskuyu khimiyu [Introduction to Theoretical Organic Chemistry], Vysshaya Shkola, Moscow, 1974, 446 pp. (in Russian).

    Google Scholar 

  33. G. A. Abakumov, V. K. Cherkasov, K. G. Shalnova, I. A. Teplova, G. A. Razuvaev, J. Organomet. Chem., 1982, 236, 333; DOI: https://doi.org/10.1016/S0022-328X(00)86907-7.

    Article  CAS  Google Scholar 

  34. A. J. Gordon, R. A. Ford, A Handbook of Practical Data, Techniques, and References, John Wiley & Sons, 1972, 560 pp.

  35. K. A. Martyanov, V. K. Cherkasov, G. A. Abakumov, M. A. Samsonov, V. V. Khrizanforova, Y. H. Budnikova, V. A. Kuropatov, Dalton Trans., 2016, 45, 7400; DOI: https://doi.org/10.1039/c6dt00769d.

    Article  CAS  Google Scholar 

  36. Data Collection, Reduction and Correction Program, CrysAlisPro 1.171.38.46 — Software Package, Rigaku OD, 2015.

  37. G. M. Sheldrick, SHELXTL. Version 6.14. Structure Determination Software Suite, Bruker AXS, Madison (WI, USA), 2003.

    Google Scholar 

  38. SCALE3 ABSPACK: Empirical absorption correction, CrysAlisPro 1.171.38.46 — Software Package, Rigaku OD, 2015.

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Authors and Affiliations

  1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603950, Nizhny Novgorod, Russian Federation

    T. N. Kocherova, N. O. Druzhkov, A. S. Shavyrin, M. V. Arsenyev, E. V. Baranov, V. A. Kuropatov & V. K. Cherkasov

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  1. T. N. Kocherova
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  2. N. O. Druzhkov
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  3. A. S. Shavyrin
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  4. M. V. Arsenyev
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  5. E. V. Baranov
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  6. V. A. Kuropatov
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  7. V. K. Cherkasov
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Correspondence to T. N. Kocherova.

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Dedicated to Academician of the Russian Academy of Sciences V. N. Charushin on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 916–924, May, 2021.

This work was financially supported by the Russian Science Foundation (Project No. 19-13-00142) using equipment of the Joint Analytical Center of the G. A. Razuvaev Institute of Organometallic Chemistry of the Russian Academy of Sciences.

No human or animal subjects were involved in this research.

The authors declare no conflict of interest, financial or otherwise.

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Kocherova, T.N., Druzhkov, N.O., Shavyrin, A.S. et al. Isopropyl-substituted o-benzoquinones and oxanthrenequinones. Effect of steric shielding of alkyl substituents on reactivity. Russ Chem Bull 70, 916–924 (2021). https://doi.org/10.1007/s11172-021-3167-6

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  • DOI: https://doi.org/10.1007/s11172-021-3167-6

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