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Synthesis of Functionalized Diorganyl Selenides from Selenium Dihalides and Allylic Aromatic Compounds

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Abstract

Hitherto unknown addition and methoxyselenation reactions of selenium dihalides with methyl eugenol and allyl naphth-1-yl ether were studied. The addition and methoxyselenation reactions of selenium dihalides with methyl eugenol led mainly to Markovnikov products, while the formation of anti-Markovnikov products prevailed in the reactions with allyl naphth-1-yl ether. Families of novel functionalized selenides, including bis[3-(3,4-dimethoxyphenyl)-2-methoxy- and -2-haloprop-1-yl] selenides, bis[3-(3,4-dimethoxyphenyl)-1-methoxy- and -1-haloprop-2-yl] selenides, bis[3-(naphth-1-yl)-1-methoxy- and -1-haloprop-1-yl] selenides, bis[3-(naphth-1-yl)-2-methoxy- and -2-haloprop-1-yl] selenides, were synthesized.

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Acknowledgments

The authors are grateful to the Baikal Analytical Center for Collective Use, Siberian Brach, Russian academy of Sciences, for spectral measurements and elemental analysis.

Funding

The work was financially supported by the Russian Foundation for Basic Research (project no. 18-03-00859_a).

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, SB, RAS, ul. Favorskogo 1, Irkutsk, 664033, Russia

    M. V. Musalov, V. A. Yakimov, V. A. Potapov, S. V. Amosova & S. V. Zinchenko

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  1. M. V. Musalov
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  2. V. A. Yakimov
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  3. V. A. Potapov
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  4. S. V. Amosova
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  5. S. V. Zinchenko
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Corresponding author

Correspondence to V. A. Potapov.

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Conflict of Interest

The authors declare no conflict of interest.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 8, pp. 1247–1254.

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Musalov, M.V., Yakimov, V.A., Potapov, V.A. et al. Synthesis of Functionalized Diorganyl Selenides from Selenium Dihalides and Allylic Aromatic Compounds. Russ J Org Chem 55, 1153–1159 (2019). https://doi.org/10.1134/S1070428019080141

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