Studies of the Oxidation of Hexabenzylhexaazaisowurtzitane

A series of oxidation reactions of hexabenzylhexaazaisowurtzitane (HBIW, 1 ) were studied. Compound 1 was treated with potassium permanganate in CH₂Cl₂ by adding Na₂CO₃ to adjust pH to 7-8 to obtain tetrabenzoyldibenzylhexaazaisowurtzitane ( 3 ) with a yield of 70%. With acetic anhydride (Ac₂O) as solvent, monoacetyltribenzoyldibenzylhexaazaisowurtzitane ( 4 ), diacetyldibenzoyldibenzylhexaazaisowurtzitane ( 5 ), triacetylmonobenzoyldibenzylhexaazaisowurtzitane ( 6 ) and tetraacetyldibenzylhexaazaisowurtzitane ( 7 ) were also obtained from the oxidation of compound 1 . The results show that only the oxidative cleavage of the cage system in compound 1 was observed in most cases. The cleavage was a cation catalysis mechanism.