Example of a Facile Substitution of the Hydroxy Group Due to the Anchimeric Assistance of Selenium

Abstract

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.