Sterically shielded primary anilides of the alkaline-earth metals of the type (thf)Ae(NH-Ar*) (Ae = Mg, Ca, Sr, and Ba; Ar* = bulky aryl).

Metalation of 2,4,6-triphenylphenylamine (HN-CH-2,4,6-Ph, 1a) and 4-methyl-2,6-bis(diphenylmethyl)aniline (2,6-bis(diphenylmethyl)--toluidine, HN-CH-4-Me-2,6-(CHPh), 2a) with dibutylmagnesium and Ae[N(SiMe)] with a stoichiometric 1 : 2 ratio in THF at room temperature yields the corresponding primary anilides [(thf)Ae{N(H)-CH-2,4,6-Ph}] (Ae/ = Mg/2 (1b), Ca/2 (1c), Sr/3 (1d), and Ba/3 (1e)) and [(thf)Ae{N(H)-CH-4-Me-2,6-(CHPh)}] (Ae/ = Mg/2 (2b), Ca/3 (2c) and Sr/2 (2d)), respectively. The 1 : 1 reaction of Mg(/Bu) and MgPh with 2a leads to the formation of heteroleptic [(thf)Mg(R){N(H)-CH-4-Me-2,6-(CHPh)}] (R = /Bu (2bBu), Ph (2bPh)). At 50 °C, the strontium complex 2d liberates one equivalent of 2a intramolecular deprotonation of the triarylmethyl functionality yielding dinuclear [(thf)Sr{N(H)-CH-4-Me-2-(CPh)-6-(CHPh)}] (2d'). The barium compound is significantly more reactive and regardless of applied stoichiometry the isotypic barium congener [(thf)Ba{N(H)-CH-4-Me-2-(CPh)-6-(CHPh)}] (2e') forms. The molecular structures of 1c, 2d, 2d', and 2e' are stabilized by metal-phenyl π-interactions.