Ambident Reactivities of Methylhydrazines


  • We thank the Deutsche Forschungsgemeinschaft (SFB 749) and the Fonds der Chemischen Industrie for financial support.


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Kinetics versus thermodynamics: Methyl groups increase the nucleophilic reactivity of the substituted position of hydrazines and reduce the nucleophilicity of the adjacent nitrogen center. As a result, the tertiary nitrogen atom of 1,1-dimethylhydrazine is 3000 times more reactive than the NH2 group, but under thermodynamic control substitution of an NH2 proton occurs (see picture).