Complete Hydrogen Transfer: Tin Hydride Reactivity toward Adamantylisonitrile and Benzonitrile

Adamantylisonitrile and benzonitrile were reacted with bulky substituted organotin trihydride [Ar*SnH3] [Ar* = (C6H3-2,6-Trip(2)), Trip = 2,4,6-triisopropylphenyl]. They do not show any reaction at room temperature as well as at 80 degrees C. After activation of the organotin trihydride with diethylmethylamine in the isonitrile case three hydrogen atoms were transferred from the tin atom to the isonitrile unit and a carbon tin bond was formed to give an intramolecular adduct between a diorganostannylene and a dialkylamine. Benzonitrile as well as adamantylisonitrile react both with low-valent organotin hydride [Ar*SnH](2). Benzonitrile shows an insertion reaction with the low-valent organotin hydride to yield a dimeric insertion product, whereas the isonitrile carbon atom of adamantylisonitrile abstracts three hydrogen atoms from the low-valent organotin hydride to give an equimolar mixture between (adamantylmethylamido)organostannylene and a bis(isonitrile)distannyne adduct.