Polar and radical bicyclizations of cyclo-oct-3-en-1-yl hydroperoxide to afford 2-functionalised-8,9-dioxabicyclo[5.2.1]decanes

8,9-Dioxabicyclo[5.2.1]decanes with bromomercurio, hydroxy, bromo, iodo, and oxo substituents at the 2-position have been prepared from cyclo-oct-3-en-1-yl hydroperoxide; the reactions include extensions of cycloperoxyiodination and of peroxyl radical cyclization to the formation of bicyclic peroxides.