Hydroperoxidation of alkanes with hydrogen peroxide catalyzed by aluminium nitrate in acetonitrile

The first example of alkane oxygenation with hydrogen peroxide catalyzed by a non-transition metal derivative (aluminium) is reported. Heating (70 degrees C) a solution of an alkane, RH, hydrogen peroxide (70% aqueous) and a catalytic amount of Al(NO3)(3)center dot 9H(2)O in air for a few hours afforded the corresponding alkyl hydroperoxide, ROOH. With cyclooctane, the hydroperoxide yield attained 31% and the maximum turnover, number was 150. It is proposed on the basis of measurements of the selectivity parameters for the oxidation of linear and branched alkanes and a kinetic study that the oxidation occurs with the participation of hydroxyl radicals. (C) 2008 Elsevier Ltd. All rights reserved.