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

Author(s)

Mandelli‚ D. ; Chiacchio‚ K.C. ; Kozlov‚ Y.N. ; Shul’pin‚ G.B.

• Document type: Journal article
• Source: Tetrahedron Letters; v. 49, n. 47, p. 6693-6697, 2008.

Abstract

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. (AU)

• FAPESP's process: 06/03984-8 - Georgiy Borisovich Shul'pin | Russian Academy of Sciences - Russia
• Grantee: Dalmo Mandelli
• Support Opportunities: Research Grants - Visiting Researcher Grant - International
• FAPESP's process: 06/03996-6 - Oxidation of organic compounds including natural products catalysed by transitions metals: Mn, Os and Cu
• Grantee: Dalmo Mandelli
• Support Opportunities: Regular Research Grants