The reductively disilylated N-heterocyclic systems 1,4-bis(trimethylsilyl)-1-aza-2,5-cyclohexadiene (1Si), 1,4-bis(trimethylsilyl)-1,4-dihydropyrazine (2Si) and its methyl derivatives (3Si and 4Si), and 1,1’-bis(trimethylsilyl)-4,4’-bipyridinylidene (5Si) are proficient organosilicon reagents owing to their low first vertical ionization...