Diacetoxylation of nonconjugated dienes with TeO2 and the isolation of intermediate organotellurium compounds

Article abstract of DOI:10.1016/0022-328X(94)05001-R

Tellurium(IV) oxide (TeO2) reacts with nonconjugated dienes in acetic acid at reflux temperature in the presence of lithium halide or iodine to give the corresponding vic-diacetates in moderate yields.When the reaction is carried out at 80 deg C and the reaction mixture is then reduced with aqueous sodium thiosulfate, bis(β-acetoxyalkyl)ditellurides are isolated as main products.Treatment of the ditellurides with refluxing acetic acid affords the corresponding vic-diacetates in good yields.The expected tellurium containing heterocyclic compounds, such as telluracyclopentanes and telluracyclohexanes, are not formed and/or isolated under the conditions employed.When 4-vinylcyclohexene and limonene are used as dienes in the diacetoxylation reaction, aromatic compounds due to the dehydrogenation of cyclohexene ring are also produced in moderate yields. Keywords: Tellurium; Oxidation; Diolefin; Lithium halide; Iodine; Diacetoxylation