Reactions of conjugated arylazocyclohexenes with Grignard reagents; X-ray crystal structure of 1-hydroperoxy-1-(o-methoxyphenylazo)-2-phenylcyclohexane

Abstract

Conjugated arylazocyclohexenes react with aromatic and aliphatic Grignard reagents to furnish 2-aryl- and 2-alkyl-cyclohexanone arylhydrazones having the syn-configuration with the 2-substituent axially oriented. Their structures have been established by chemical and spectroscopic methods. These compounds, as well as the anti-isomers, undergo ready autoxidation to give arylazo-hydroperoxides. The structure of 1-hydroperoxy-1-(o-methoxyphenylazo)-2-phenylcyclohexane has been determined by X-ray analysis.