The tetradentate, trianionic ligand tris(pyrrolyl-alpha-methyl)amine (H(3)tpa) is available in 84% yield in a single step by a triple Mannich reaction involving 3 equiv of pyrrole, 3 equiv of formaldehyde, and ammonium chloride. The new ligand is readily placed on titanium by transamination on Ti(NMe2)(4), which generates Ti(NMe2)(tpa) (1) in 73% yield. Treating 1 with 1 equiv of 1,3-dimethyl-2-iminoimidazolidine (H-imd) in toluene provided a rare example of a titanium 2-iminoimidazolidinide, which displays some interesting structural features. Of note is the Ti-N(imd) distance of 1.768(2) Angstrom, a typical Ti-N double to triple bond distance. Reaction of Zr(NMe2)(4) with H(3)tpa gave a complex of variable composition, probably varying in the amount of labile dimethylamine retained. However, stable discreet compounds were available by addition of THF, pyridine, or 4,4'-di-tert-butyl-2,2'-bipyridine (Bu(t)bpy) to in situ generated Zr(NMe2)(NHMe2)(x)(tpa). Three chloro zirconium complexes were generated using three different strategies. Treating Zr(tpa)(NMe2)(Bu(t)bpy) (5) with ClSiMe3 afforded Zr(tpa)(Cl)(Bu(t)bpy) (6) in 92% yield. Reaction of Li(3)tpa with ZrCl4-(THF)(2) in THF gave a 72% yield of ZrCl(tpa)(THF)(2) (7). In addition, treatment of ZrCl(NMe2)(3) with H(3)tpa cleanly generated ZrCl(NHMe2)(2)(tpa) (8) in 95% yield. An organometallic zirconium complex was generated on treatment of 6 with LiCequivalent toCPh; alkynyl Zr(Cequivalent toCPh)(tpa)(Bu(t)bpy) (9) was isolated in 62% yield. 1, Ti(imd)(tpa) (2), 6, and 9 were characterized by X-ray diffraction.