Abstract
1-Aryl-1-phenylethane hydroperoxides (APE-HPO) were decomposed in the presence of sulfuric acid to give phenol, substituted phenols, acetophenone, and substituted acetophenones. The effect of a variety of substituents on the ratios of cited four kinds of products was investigated. The decomposition of APE-HPO, having an electron-donating substituent, gave much more substituted phenols and acetophenone than phenol and substituted acetophenones. The decomposition rates of APE-HPO, having various substituents, followed a Hammett relationship with a negative ρ value, -1.23 and it became apparent that the product distributions and the rates are controlled by the electron-donating magnitude of a substituent in the acid-decomposition of APE-HPO.
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