The cleavage of methylene and ethylene bridges between aromatic moieties is a reaction relevant to coal liquefaction. To model this reaction, the decomposition of a polyfunctional organic molecule, 4-(1-naphthylmethyl)bibenzyl, I, was studied under thermal and catalytic reaction conditions. The thermal reaction of compound I proceeds only at temperatures above 400 o C. In the presence of high surface area carbon blacks, however, bond cleavage takes place at temperatures as low as 320 o C. The presence of carbon black results in not only higher overall conversion but extremely selective cleavage of a specific bond of compound I. Certain kinetic parameters for thermal and catalytic cleavage reactions of I were determined. Preliminary mechanistic studies indicate that an electron-transfer pathway may be operative in the carbon black catalyzed reactions of compound I