The Stereochemistry of Autoxidation of Methylcyclohexanes

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概要

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• Autoxidation of 1, <I>c</I>-3, <I>c</I>-5- or 1, <I>c</I>-3, <I>t</I>-5-trimethylcyclohexane with oxygen in the presence of azobisisobutyronitrile at 60°C and subsequent reduction with lithium aluminium hydride gave 1, <I>t</I>-3, <I>t</I>-5- and 1, <I>c</I>-3, <I>c</I>-5-trimethyl-<I>r</I>-1-cyclohexanol in the same ratio of 1/0.85. Such an almost random attack of oxygen on both sides of intermediate methylcyclohexyl radicals was also observed in autoxidation of 1,2-dimethyl-, 1,4-dimethyl-, and 1,1,3,5-tetramethylcyclohexanes. Approximate relative reactivities of tertiary hydrogens in various steric environments in methylcyclohexanes towards abstraction were determined. Steric effects on the attack of oxygen and the abstraction of hydrogen are discussed.

• 公益社団法人 日本化学会の論文

著者

• Simamura Osamu

  Department of Chemistry Faculty of Science The University of Tokyo

• Miyajima Shingo

  Department of Applied Chemistry, Faculty of Engineering, Toyo University

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