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Synthesis of unsaturated organoselenium compounds via the reaction of organic diselenides with 2,3-dichloro-1-propene in the hydrazine hydrate-KOH system

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Abstract

Dimethyldiselenide reacts with 2,3-dichloro-1-propene at 20–25°C in the hydrazine hydrate-KOH medium to form 2-chloro-3-methylselanyl-1-propene with 90% yield. Diphenyldiselenide in the reaction with 2,3-dichloro-1-propene, depending on the conditions, can give quite selectively four products: 2-chloro-3-phenylselanyl-1-propene, phenylselanylpropadiene, 1-phenylselanyl-1-propyne, and Z-1,2-bis(phenylselanyl)-1-propene. The effect of the selenium atom on the reaction direction and the products structure is discussed.

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Authors and Affiliations

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

    E. P. Levanova, V. A. Grabel’nykh, V. S. Vakhrina, N. V. Russavskaya, A. I. Albanov, L. V. Klyba, O. A. Tarasova, I. B. Rozentsveig & N. A. Korchevin

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  1. E. P. Levanova
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  2. V. A. Grabel’nykh
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  3. V. S. Vakhrina
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  4. N. V. Russavskaya
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  5. A. I. Albanov
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  6. L. V. Klyba
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  7. O. A. Tarasova
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  8. I. B. Rozentsveig
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  9. N. A. Korchevin
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Correspondence to V. A. Grabel’nykh.

Additional information

Original Russian Text © E.P. Levanova, V.A. Grabel’nykh, V.S. Vakhrina, N.V. Russavskaya, A.I. Albanov, L.V. Klyba, O.A. Tarasova, I.B. Rozentsveig, N.A. Korchevin, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 9, pp. 1434–1439.

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Levanova, E.P., Grabel’nykh, V.A., Vakhrina, V.S. et al. Synthesis of unsaturated organoselenium compounds via the reaction of organic diselenides with 2,3-dichloro-1-propene in the hydrazine hydrate-KOH system. Russ J Gen Chem 83, 1660–1665 (2013). https://doi.org/10.1134/S1070363213090065

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  • DOI: https://doi.org/10.1134/S1070363213090065

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