The Decomposition of Cyclohexyl Hydroperoxide in the Presence of Cyclohexanone and a Novel Rearrangement Product
- 1 March 1969
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 42 (3) , 789-794
- https://doi.org/10.1246/bcsj.42.789
Abstract
One of the major reaction products besides cyclohexanol from the reaction of cyclohexyl hydro-peroxide with cyclohexanone was isolated and confirmed as ε-cyclohexyloxycaproic acid. The rate of formation of ε-cyclohexyloxycaproic acid was measured in excess cyclohexanone and found to follow a first order law for cyclohexyl hydroperoxide. The activation energy of 10.1 kcal/mol was found for the formation of the acid. The rate of decomposition of cyclohexyl hydroperoxide in cyclohexane was measured in the presence of various concentrations of cyclohexanone and the rates of formation of cyclohexanol and the free carboxylic acids were also measured. An adduct formation between cyclohexyl hydroperoxide and cyclohexanone followed by homolytic decomposition of the adduct was suggested to explain the experimental results.Keywords
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