1,1,1-Trimethylhydrazinium Iodide: A Novel, Highly Reactive Reagent for Aromatic Amination via Vicarious Nucleophilic Substitution of Hydrogen
Philip F. Pagoria,* Alexander R. Mitchell and Robert D. Schmidt
*Lawrence Livermore National Laboratory 7000 East Avenue, Livermore, CA 94550, Email: pagoria1llnl.gov
P. F. Pagoria, A. R. Mitchell, R. D. Schmidt, J. Org. Chem., 1996, 61, 2934-2935.
TMHI, that is easily prepared from 1,1-dimethylhydrazine, is a novel aminating reagent for vicarious nucleophilic substitution. It can be used to obtain isomers not produced by reaction with other nucleophilic aminating reagents.
see article for more examples
proposed, simplified mechanism
vicarious nucleophilic substitution, amination