Iron(III)-Catalyzed Dimerization of Cycloolefins: Synthesis of High-Density Fuel Candidates

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Bicycloalkanes with the potential for deployment in high-density diesel and jet fuels can be conveniently generated from cycloolefins using a two-step process. Dimerization of the cycloolefin may be affected, catalytically, using commercially available Fe(III) salts, and the reaction is tolerant of ring size (C5–C8) and limited ring-substitution patterns. Generation of an allylic radical is strongly suggested; however, observation of Fe-catalyzed olefin rearrangements and transfer dehydrogenation reactions may implicate the involvement of discrete organometallic complexes in the reaction. The fully saturated bicycloalkanes are easily prepared via metal-catalyzed hydrogenation of the cycloolefin–cycloalkane dimeric species.