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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.

DOI: 10.1021/jo952257z (free Supporting Information)


Abstract

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.

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proposed, simplified mechanism



Key Words

vicarious nucleophilic substitution, amination


ID: J42-Y1996-640