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Alkoxylation of 3,6-di-tert-butyl-1,2-benzoquinone. New bis-1,2-benzoquinones

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Abstract

Alkoxylation of 3,6-di-tert-butyl-1,2-benzoquinone with a number of diols, including propane-1,3-diol, butane-1,4-diol, di-, and triethylene glycols, and cyclohexane-1,4-diyldimethanol, was studied. Nine new 4-alkoxy-3,6-di-tert-butyl-1,2-benzoquinones were synthesized, four of which were bis-1,2-benzoquinones with different tethers (6–13 atoms) between the quinone fragments. Depending on the length of the chain between the hydroxy groups in glycols, bicyclic 4,5-disubstituted 3,6-di-tert-butyl-1,2-benzoquinones were formed or their stepwise alkoxylation occurred. The newly synthesized o-benzoquinone derivatives can be reduced with alkali metals to give radical anions and converted into semiquinone chelates with manganese carbonyl.

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Authors and Affiliations

  1. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, ul. Tropinina 49, Nizhnii Novgorod, 603950, Russia

    M. P. Shurygina, N. O. Druzhkov, M. V. Arsen’ev, M. P. Bubnov, G. K. Fukin, S. A. Chesnokov & V. K. Cherkasov

Authors
  1. M. P. Shurygina
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  2. N. O. Druzhkov
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  3. M. V. Arsen’ev
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  4. M. P. Bubnov
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  5. G. K. Fukin
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  6. S. A. Chesnokov
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  7. V. K. Cherkasov
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Corresponding author

Correspondence to S. A. Chesnokov.

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Original Russian Text © M.P. Shurygina, N.O. Druzhkov, M.V. Arsen’ev, M.P. Bubnov, G.K. Fukin, S.A. Chesnokov, V.K. Cherkasov, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 4, pp. 490–498.

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Shurygina, M.P., Druzhkov, N.O., Arsen’ev, M.V. et al. Alkoxylation of 3,6-di-tert-butyl-1,2-benzoquinone. New bis-1,2-benzoquinones. Russ J Org Chem 47, 486–495 (2011). https://doi.org/10.1134/S1070428011040038

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  • DOI: https://doi.org/10.1134/S1070428011040038

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