Aryliminodimagnesium Reagents. IV. The Independent Preparation of Unsymmetrically Substituted Azoxyarene Isomers and Their Deoxygenation

Abstract

Abstract By use of the condensation reaction of aryliminodimagnesium reagents (ArN(MgBr)2) with nitroarenes, six symmetrical and eight unsymmetrical azoxyarenes including four pairs of isomers were prepared in 40–80% yields. The deoxygenation reaction of the azoxyarenes by treating with five molar equivalents of p-MeOC6H4N(MgBr)2 at 55 °C in tetrahydrofuran was also studied, and the reactivity of deoxygenation was correlated to the shift of the electronic absorption maximum of azoxyarene.