Abstract Twofold hydrogen/metal interconversions (" dimetalations") can be accomplished with “spiny” arenes (tert-butylbenzene, 1, 4-di-tert-butylbenzene, 1, 1, 3, 3-tetramethylindane and congeners) and N, N-crowded anilines (2, 2, 6, 6-tetramethyl-1-phenylpiperidine and N, N-bis [triethylsilyl] aniline), albeit incompletely (average and optimum yields of trapping products 25% and 41%, respectively). All the evidence points at an aggregate ...