Abstract
The first representative of a new class of organoselenium bicyclic compounds, 7,8-dimethoxy-9-selenabicyclo[4.2.1]nonane, was prepared by the iodine-mediated reaction of elemental selenium and 1,3-cyclooctadiene. Comparative kinetics of the oxidation of 7,8-dimethoxy-9-selenabicyclo[4.2.1]nonane 1 and its isomer 2,6-dimethoxy-9-selenabicyclo[3.3.1]nonane 2 were studied by 1H NMR spectroscopy and found to be dozens of times faster for the former. The catalytic activity of 7,8-dimethoxy-9-selenabicyclo[4.2.1]nonane 9-oxide formed in situ from 1 and simulating the GPx-like activity in oxidation of thiols by H2O2 in MeOH, is shown to be higher than that of the isomeric 2,6-dimethoxy-9-selenabicyclo[3.3.1]nonane 9-oxide.
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