A Convenient, One-Pot Preparative Method for Tri- and Tetrasubstituted Hydrazines from Azobenzenes and Organolithiums

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Abstract
Organolithiums add smoothly to the N=N bond of azobenzenes at -78°C to give the lithium derivative of the trisubstituted hydrazine. The corresponding trisubstituted hydrazines, or a variety of unsymmetrically tetrasubstituted hydrazines, were thus conveniently prepared in high yielding one-pot procedures by direct quench, or by treatment of the reaction mixture with an alkyl iodide prior to workup.

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