The Liquid Phase Oxidation of trans-Decahydronaphthalene in Acetic Anhydride

Abstract

The oxidation of trans-decahydronaphthalene [1] was carried out in acetic anhydride with oxygen in the presence of transition metal salts and bromide.
The oxidation of [1] in acetic anhydride proceeded much more rapidly than that in acetic acid. The most active catalyst system was Co-Ce-NH₄Br. The proper range of Ce/Co ratio, Br/Me ratio(Me=Co+Ce), and total metal concentration were 0.005-1.0, 1.0-2.0, and 3.5-7.0x10^-2 (mol/l), respectively.
The main componen t of monosubstituted oxidation products of [1] was 2-substituted calones. Decahydronaphthyl acetates [2] were formed by the oxidation of [1] in acetic anhydride by one step and the selectivity of [2] was above 80 mol% at 120°C.
In addition, relative reactivities of hydrogen atoms of [1] were determined at temperatures from 90 to 120°C.