The oxidative addition of a variety of group 13 and group 14 halides and alkyls R(a)MX to the mono valent group 13 bis-imidinate Ga(DDP) (DDP = 2-((2,6-diisopropyl-phenyl)amino)-4-1(2,6-diisopropylphenyl)iminol-2-pentene) is reported. Accordingly, the insertion of Ga(DIDP) into the Ga-Me bond of GaMe(3) yield in the complexes [{(DDP)GaMe)GaMe(2)] (1) and [{(DDP)GaMe}(2)GaMe] (2), respectively, which show a temperature-dependent equilibrium between 1 at higher temperatures and 2 at lower temperatures. In the case of GaCl(3), the only isolable product is [{(DDP)GaCl}(2)GaCl) (3). The related reaction of SnMe(2)Cl(2) with Ga(DDP) yields the compound [Me(2)Sn(ClGa(DDP)}(2)] (4), whereas SnMe(4) behaves inert. In the case of SiCl(4), only the monoinsertion product [Cl(3)Si(ClGa(DDP)}] (5) was observed. Finally, [(CH(3))(3)C(ClGa(DDP)}] (6) is synthesized by insertion of Ga(DDP) into the C-Cl bond of ClC(CH(3))(3). All new compounds were fully characterized by elemental analysis, NMR-spectroscopy, and single-crystal X-ray diffraction analysis.