Example of a Facile Substitution of the Hydroxy Group Due to the Anchimeric Assistance of Selenium
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Bis(2-bromo-3-hydroxypropyl) selenide was synthesized in quantitative yield by the reaction od selenium bromide with allyl alcohol. The product undergoes facile methanolysis at room temperature, which is accompanied by a rearrangement and involves substitution of bromine and hydroxy groups, located β to the selenium atom, to form bis(1,3-dimethoxypropan-2-yl) selenide and (3-hydroxy-2-methoxypropyl)(1,3-dimethoxypropan-2-yl) selenide.
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- 12.Reutov, O.A., Kurts, A.L., and Butin, K.P., Organicheskaya khimiya (Organic Chemistry), Moscow: Binom. Laboratoriya Znanii, 2005, vol. 2, p. 244.Google Scholar