Conversion of 3-cyclopentenyl hydroperoxide into 5-substituted-2,3-dioxabicyclo[2.2.1]heptanes

3-Cyclopentenyl hydroperoxide $\text{8}$ has been prepared from cyclopentadiene via hydroboration and autoxidation. Bromination of $\text{8}$ followed by treatment with an appropriate silver salt has afforded the 5-substituted-2,3-dioxabicyclo2.2.1] heptanes $\text{11}$ ($\text{endo}$-bromo), $\text{13}$ ($\text{exo}$-bromo), and $\text{12}$ ($\text{exo}$-trifluoroacetoxy).