In 1934, Suszko and Schillak reported that the treatment of dibenzo[g,p]chrysene (DBC; 1a) with sodium dichromate results in the oxidative cleavage of the inner double bond, yielding tetrabenzocyclodecan-1,6-dione (2a) (Figure ). In 1980, the X-ray crystal structure of 2a was reported. However, the figure-eight structure of 2a has arguably been under-appreciated so far, and detailed, systematic investigations into its chemistry have not yet been conducted. In this study, we have revisited the chemistry of the oxidative cleavage of the inner double bond of DBC and examined its utility with regard to the scope of the transformation and the fundamental properties of the products of this reaction, thus establishing a constructive destruction approach. Constructive destruction should be thought of as an internal-modification strategy of conjugated π-systems in the same vein as molecular surgery, a research area which also remains underexplored so far. We have also named tetrabenzocyclodecan-1,6-dione 2a 'eightphenone' in light of its beautiful figure-eight structure that consists of two benzophenone subunits.