Sterically shielded primary anilides of the alkaline-earth metals of the type (thf) n Ae(NH-Ar*) 2 (Ae = Mg, Ca, Sr, and Ba; Ar* = bulky aryl).

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