The iodine-assisted hydroxyselenenylation of alkenes with elemental selenium

β,β′-Dihydroxy selenides are obtained by the iodine-assisted reaction of elemental selenium with alkenes in aqueous acetonitrile in up to 83% yield and ∼1: 1 diastereomeric ratio. The X-ray analysis of bis(2-hydroxycyclohex-1-yl) selenide revealed it to be the trans,trans-isomer indicating that the reaction occurred stereoselectively as anti-addition.