Reactions of conjugated arylazocycloalkenes with Grignard reagents. Part 3. A convenient synthesis of 2,6-diaryl- and 2-alkyl-6-aryl-cyclohexanones

Abstract

A synthesis of the title compounds with the substituents at C-2 and C-6 trans to each other is described. 2-Aryl-cyclohexanones were converted into 1-phenylazo-6-arylcyclohexenes, which by reaction with Grignard reagents led to trans-2,6-diaryl- and trans-2-alkyl-6-aryl-cyclohexanone phenylhydrazones. These compounds by oxidative hydrolysis furnished the corresponding trans-ketones, which were readily epimerised into the more stable cis-isomers.