Abstract: The oxidation of pentacyclo5. 4. 0. 02, 6. 03,10. 05,9 undecane-8, 11-dioxime 2 and pentacyclo 6. 3. 0. 02 6. 02,10. 05,9 undecane-4, 7-dioxime 8 is studied. It was found that direct oxidation on the two oximes has not been successful. However, the best oxidant for 2 is NBS, and for 8, the best method is a two-step reaction using bromine and ozone.