Abstract
Abstract A drastic deviation from the usually accepted reaction path was observed when oxidation of olefins was carried out in acetic acid with selenium dioxide in the presence of concentrated sulfuric acid. Oxidation of cyclohexene gave a mixture of cis- and trans-1,2-diacetoxycyclohexane. It was shown that in the oxidation of cyclohexene the organoselenium intermediate which produced 3-acetoxy-1-cyclohexene on pyrolysis, is not the intermediate in the present reaction. A study on reaction variables, such as effect of molar ratio of cyclohexene to selenium dioxide, amount of sulfuric acid, and water, reaction time and temperature, was undertaken. The reaction was extended to 1-octene and 1-hexene. A general structure for the organoselenium compound produced in the oxidation of terminal olefins in acetic acid without sulfuric acid, has been proposed. On the basis of our data and some previous concepts a reaction scheme has also been given.
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