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Synthesis of bis(2-haloalkyl) selanes and selenides based on selenium dioxide and terminal alkenes

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Abstract

Selenium tetrahalides generated from selenium dioxide and hydrogen halides (HCl, HBr) reacted with hex-1-ene, hept-1-ene, and oct-1-ene at a SeO2‒alkene molar ratio of 1: 2 to give mixtures of dihalobis-(2-haloalkyl)-λ4-selanes (yield 80‒90%) and bis(2-haloalkyl) selenides (yield 5‒12%). Halogenation of the resulting mixtures afforded 85‒93% (calculated on the initial SeO2) of the corresponding dihalobis(2-haloalkyl)-λ4-selanes, and the reduction of the same mixtures with Na2S2O5 gave bis(2-haloalkyl) selenides in 80‒86% yield. In the reaction with a SeO2‒alkene ratio of 5: 8, pure dihalobis(2-haloalkyl)-λ4-selanes were formed in 84‒93% yield. Dichlorobis(2-chloro-2-phenylethyl)-λ4-selane was obtained in 72% yield in the reaction of SeO2‒HCl with styrene.

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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

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

Authors
  1. M. V. Musalov
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  2. E. O. Kurkutov
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  3. V. A. Potapov
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  4. A. G. Khabibulina
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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 © M.V. Musalov, E.O. Kurkutov, V.A. Potapov, A.G. Khabibulina, A.I. Albanov, S.V. Amosova, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 12, pp. 1774–1779.

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Musalov, M.V., Kurkutov, E.O., Potapov, V.A. et al. Synthesis of bis(2-haloalkyl) selanes and selenides based on selenium dioxide and terminal alkenes. Russ J Org Chem 53, 1809–1814 (2017). https://doi.org/10.1134/S1070428017120041

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  • DOI: https://doi.org/10.1134/S1070428017120041

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