REACTIONS OF CONJUGATED ARYLAZOCYCLOHEXENES WITH GRIGNARD-REAGENTS .2. NEW STEREOSPECIFIC ROUTE TO 2-ALKYL-CYCLOHEXANONES AND 2-ARYL-CYCLOHEXANONES

4-Methyl- and 4-t-butyl-1-arylazocyclohexenes react with aliphatic and aromatic Grignard reagents, to furnish, after oxidative hydrolysis of the intermediate arylhydrazones, 2-alkyl-4-methyl-, 2-aryl-4-methyl-, 2-alkyl-4-t-butyl-, and 2-aryl-4-t-butyl-cyclohexanones, with a trans-configuration. From the reactions with o-tolyl- and α-naphthyl- magnesium bromide only the cis-isomers were obtained. The structures of the products were determined by spectroscopic methods and by epimerization of the trans-cyclohexanones into the more stable cis-isomers.