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

Article abstract of DOI:10.1246/bcsj.56.203

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 40-80percent yields.The deoxygenation reaction of the azoxyarenes by treating with five molar equivalents of p-MeOC6H4N(MgBr)2 at 55 deg C in tetrahydrofuran was also studied, and the reactivity of deoxygenation was correlated to the shift of the electronic absorption maximum of azoxyarene.