Journal of Organometallic Chemistry p. 217 - 231 (2015)
Update date:2022-08-16
Topics:
Shul'pina, Lidia S.
Kudinov, Aleksandr R.
Mandelli, Dalmo
Carvalho, Wagner A.
Kozlov, Yuriy N.
Vinogradov, Mikhail M.
Ikonnikov, Nikolay S.
Shul'pin, Georgiy B.
The efficient (turnover numbers attained 1200) oxidation of alkanes to the corresponding alkyl hydroperoxides by H2O2 in the presence of catalytic amounts of ferrocene proceeds in MeCN at 40-50 °C. Benzene is oxidized in the same system to phenol. An obligatory component of the catalytic system for both reactions is pyrazine-2-carboxylic acid (PCA) or trifluoroacetic acid (TFA). Kinetic study as well as selectivity parameters testified that the oxidation proceeds with the participation of hydroxyl radicals. In the case of PCA as a co-catalyst the initial rate W0 of the reaction with both cyclohexane and benzene depends quadratically on [Cp2Fe]0 whereas the two reactions in the presence of TFA are of half order in ferrocene. The ferrocene-catalyzed reaction of cyclohexane with H2O216 in an atmosphere of labeled 18O2 gave after 2 h a mixture of labeled and unlabeled cyclohexyl hydroperoxide (total yield 20% based on starting cyclohexane) containing up to 69% of 18O (the analysis was after reduction of cyclohexyl hydroperoxide into cyclohexanol with PPh3).
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