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

Article abstract of DOI:10.1016/S0040-4039(00)97886-9

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.