Kinetics and Mechanism for the Elimination of Hydrogen between Dimethylaluminum Hydride and N-Methylaniline.
STATE UNIV OF NEW YORK AT BUFFALO DEPT OF CHEMISTRY
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The rate of elimination of hydrogen from dimethylaluminum hydride and N-methylaniline has been measured at -63 deg. in toluence solution. Reaction conditions include equal concentrations of dimethylaluminum hydride and the amine, and pseudo first order conditions with excess amine. The kinetic data are consistent with a second order rate law which is complicated by an equilibrium. The following steps of the mechanism determine the rate of elimination of hydrogen. HCH32A1 NC6H5CH3H yield HCH32A1NC6H5CH3H HCH32A1 NC6H5CH3H yield H2 CH32A1NC6H5CH3. Results are consistent with the conclusion that adduct formation is a dead end path for the elimination reaction. The elimination reaction is not a reaction of a performed adduct. The factors responsible for the formation of only a dimeric aluminum-nitrogen product, CH32A1NC6H5CH32, and the predomiance of the cis isomer over the trans 8020 are discussed.
- Organic Chemistry
- Physical Chemistry