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. Copyright.