Mechanistic investigations of iron/sulfur-catalyzed bond scission in aromatic hydrocarbons. A catalytic hydrogen atom transfer step involving a late transition state

The mechanism of carbon-carbon bond scission by 'iron sulfide' catalysts is explored through the use of substituted diphenylmethane model compounds. The reaction kinetics are shown to be first order in model compound with the methylene-arene carbon-carbon bond adjacent to the most substituted arene being selectively cleaved. These results are consistent with the catalyst acting as a hydrogen atom transfer agent.