The transfer of hydrogen from excess 9,10‐dihydroanthracene (DHA) to acceptors such as α‐methylstyrene is catalyzed, i.e. occurs at temperatures in the range 200–260 °C instead of 280–320 °C, when hydrocarbons with weaker C–H bonds than DHA, e.g. 6H‐benzo[cd]pyrene (4), 7H‐dibenzo[a,kl]anthracene (5), 4‐methyl‐7H‐benzo[de]naphthacene (6) or 8H‐dibenzo[b,fg]pyrene (7), are added to the reaction mixture. The reactions are initiated by bimolecular H‐atom transfer from 4–7 to the acceptor (retrodisproportionation) and proceed by nonchain radical mechanisms. This is supported by isotopic labelling and kinetic isotope effects, substituent and solvent effects, EPR spectroscopy of intermediate radicals, and by a comparison of the thermochemical and kinetic characteristics of these reactions.
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