Abstract
Alkoxyselenation of vinylbenzenes with selenium dihalides was accomplished for the first time. The reaction with selenium dibromide was the most efficient. Selenium dibromide reacted with vinylbenzene and 1-chloro-4-(prop-1-en-2-yl)benzene in chloroform or methylene chloride in the presence of methanol or ethanol to give the corresponding Markovnikov adducts, bis(2-alkoxy-2-phenylethyl) selenides and bis[2-alkoxy-2-(4-chlorophenyl)propyl] selenides in 82–95% yield with high regioselectivity. Bis(2-halo-2-phenylethyl) selenides can be obtained at low temperature (–60°C).
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Original Russian Text © V.A. Potapov, A.G. Khabibulina, M.V. Musalov, A.I. Albanov, S.V. Amosova, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 3, pp. 326–329.
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Potapov, V.A., Khabibulina, A.G., Musalov, M.V. et al. Reactions of selenium dihalides with vinylbenzenes. Russ J Org Chem 53, 322–325 (2017). https://doi.org/10.1134/S1070428017030022
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DOI: https://doi.org/10.1134/S1070428017030022