OXIDATION OF 1,4-DIMETHYLCYCLOHEXANE BY PERCHLORIC-ACID CATALYZED BY POLYPHENYLFERROSILOXANE

The reaction of oxidation of 1,4-dimethylcyclohexane (DMCH) by perchlo ric acid at similar to 20 degrees C catalyzed by polyphenylferrosiloxa ne has been found. The chromatographic analysis has revealed the forma tion of several products, including the tertiary alcohol with 100% ret ention of the configuration of the initial configuration. The specific feature of the process is the following: along with the high stereosp ecific formation of the tertiary alcohol, cis-trans isomerization in t he starting 1,4-DMCH is observed. The data obtained are discussed on t he basis of the mechanism, including the formation of a ferryl interme diate with the subsequent transfer of the oxygen atom to the tertiary C-H bond of 1,4-DMCH through the intermediate complex with the five-co ordinated carbon.