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Synthesis of new functionalized organoselenium compounds by heterocyclization of selenium dihalides with pent-4-en-1-ol

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Abstract

The reaction of selenium dihalides with pent-4-en-1-ol has been carried out for the first time. Efficient procedures for the synthesis of previously unknown bis(tetrahydrofuran-2-ylmethyl) selenide, dihalobis( tetrahydrofuran-2-ylmethyl)-λ4-selanes, and bis(tetrahydrofuran-2-ylmethyl) selenoxide have been developed on the basis of this reaction. The product structures have been studied by 1H, 13C, and 77Se NMR. Bis(tetrahydrofuran-2-ylmethyl) selenide and dihalobis(tetrahydrofuran-2-ylmethyl)-λ4-selanes represent equimolar mixtures of two diastereoisomers which display different signals in the 13C and 77Se NMR spectra. The oxidation of bis(tetrahydrofuran-2-ylmethyl) selenide with sodium periodate in methanol leads to the corresponding selenoxide consisting of 4 diastereoisomers.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    V. A. Potapov, M. V. Musalov, E. O. Kurkutov, M. V. Musalova, A. I. Albanov & S. V. Amosova

Authors
  1. V. A. Potapov
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  2. M. V. Musalov
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  3. E. O. Kurkutov
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  4. M. V. Musalova
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  5. A. I. Albanov
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  6. S. V. Amosova
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Corresponding author

Correspondence to S. V. Amosova.

Additional information

Original Russian Text © V.A. Potapov, M.V. Musalov, E.O. Kurkutov, M.V. Musalova, A.I. Albanov, S.V. Amosova, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 3, pp. 360–363.

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Potapov, V.A., Musalov, M.V., Kurkutov, E.O. et al. Synthesis of new functionalized organoselenium compounds by heterocyclization of selenium dihalides with pent-4-en-1-ol. Russ J Org Chem 52, 339–342 (2016). https://doi.org/10.1134/S1070428016030088

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  • DOI: https://doi.org/10.1134/S1070428016030088

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