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

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.