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Oxidation and halogenation of divinyl selenide. first synthesis of divinyl selenoxide

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Abstract

Efficient procedure was developed for the preparation of divinyl selenoxide in 92% yield by oxidation of divinyl selenide with sodium periodate. At the action of S-nucleophiles on the divinyl selenoxide it is reduced to divinyl selenide. The reaction of divinyl selenide with an equimolar amount of sulfuryl chloride or bromine led to halogenation products at the selenium atom: divinylselenium dichloride and divinylselenium dibromide. A rearrangement was discovered of divinylselenium dibromide into vinyl(1,2-dibromoethyl)-selenide. The hydrolysis of divinylselenium dichloride results in divinyl selenide.

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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

    E. O. Kurkutov, V. A. Potapov & S. V. Amosova

Authors
  1. E. O. Kurkutov
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  2. V. A. Potapov
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  3. S. V. Amosova
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Corresponding author

Correspondence to S. V. Amosova.

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Original Russian Text © E.O. Kurkutov, V.A. Potapov, S.V. Amosova, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 5, pp. 640–643.

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Kurkutov, E.O., Potapov, V.A. & Amosova, S.V. Oxidation and halogenation of divinyl selenide. first synthesis of divinyl selenoxide. Russ J Org Chem 52, 624–627 (2016). https://doi.org/10.1134/S107042801605002X

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  • DOI: https://doi.org/10.1134/S107042801605002X

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