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5-Hydroxy-2,3-dihydrobenzofuran-derived polyfunctional antioxidants 2. Synthesis of 2-dodecylselenomethyl-5-hydroxy-2,3-dihydrobenzofurans and their antioxidant profile versus 2-dodecylthiomethyl-substituted analogs

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Abstract

A number of 2-dodecylselenomethyl-5-hydroxy-2,3-dihydrobenzofurans were synthesized from the corresponding 5-alkoxy-2-iodomethyl-substituted derivatives. The rate constants of the reaction with peroxide radicals and stoichiometric coefficients of inhibition were measured for the synthesized compounds and their 2-dodecylthiomethyl substituted analogs in the model reaction of initiated styrene oxidation. The dissociation energies of O–H bond were also calculated. 2-Dodecylselenomethyl-5-hydroxy-2,3-dihydrobenzofurans exceed their sulfurcontaining analogs and tocopherols by antioxidant activity in the thermal autooxidation of methyl oleate by a factor of 9–14 and 19–20, respectively.

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Authors and Affiliations

  1. Novosibirsk State Pedagogical University, 28 ul. Vilyuiskaya, 630126, Novosibirsk, Russian Federation

    S. E. Yagunov, S. V. Kholshin, N. V. Kandalintseva & A. E. Prosenko

  2. Novosibirsk Research Institute of Antioxidant, 54a Krasnyi prosp., 630091, Novosibirsk, Russian Federation

    N. V. Kandalintseva & A. E. Prosenko

Authors
  1. S. E. Yagunov
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  2. S. V. Kholshin
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  3. N. V. Kandalintseva
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  4. A. E. Prosenko
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Correspondence to S. E. Yagunov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 0844–0851, May, 2018.

For Part 1, see Ref. 1

In memory of Prof. Evgeny Denisov.

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Yagunov, S.E., Kholshin, S.V., Kandalintseva, N.V. et al. 5-Hydroxy-2,3-dihydrobenzofuran-derived polyfunctional antioxidants 2. Synthesis of 2-dodecylselenomethyl-5-hydroxy-2,3-dihydrobenzofurans and their antioxidant profile versus 2-dodecylthiomethyl-substituted analogs. Russ Chem Bull 67, 844–851 (2018). https://doi.org/10.1007/s11172-018-2148-x

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  • DOI: https://doi.org/10.1007/s11172-018-2148-x

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