O- and S-Functionalized 6-Selenabicyclo[3.2.1]octanes from Elemental Selenium and 4-Vinylcyclohexene

A highly stereo- and regioselective approach to O- and S-functionalized 6-selenabicyclo[3.2.1]octanes as new types of bicyclic organoselenium compounds is developed based on the iodine-mediated reaction of elemental selenium with 4-vinylcyclohexene in the presence of O- and S-nucleophiles under mild conditions. The reaction represents the first example of simultaneous C-S and C-Se functionalization of different C═C double bonds using elemental selenium.