Carbodiimide Insertion into Organoaluminum Compounds and Thermal Rearrangement of the Products

A series of carbodiimide insertion products were prepared using various aluminum reagents (viz., AlR 3 (R = Me, Et), AlX 2 Y (X = Cl, R; Y = Cl, NR‘ 2 )) and 1,3-diisopropyl- and 1,3-di- tert -butylcarbodiimides in various stoichiometric ratios. The resulting products 1 − 20 were isolated either as colorless liquids or as solids. These compounds were characterized by 1 H NMR, 13 C NMR, IR, and mass spectral data. Elemental analysis data for some of the representative compounds were obtained. The crystal structures of two of the compounds (compounds 8 ‘‘ and 10 ) were determined by single-crystal X-ray diffraction. The competitive migration of the alkyl, chloro, or amino group attached to the aluminum atom onto the carbon of the carbodiimide is also reported.