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Updated: Sep 24, 2025

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
Published on: December 16, 2022
Selective Wacker type oxidation of a macrocyclic diene to the corresponding monounsaturated ketone used as fragrance
Tom Brunzel1, Johannes Heppekausen2, Johannes Panten2
1Leibniz Institute for Catalysis at the University of Rostock Albert-Einstein-Straße 29a 18059 Rostock Germany angela.koeckritz@catalysis.de.
Abstract:
A selective reaction method for the efficient conversion of an isomeric mixture of 1,9-cyclohexadecadiene (1,9-CHDD) to the corresponding monounsaturated cyclohexadec-8-en-1-one (8-CHD) is described. 8-CHD was synthesized via Wacker type oxidation at room temperature using a highly electrophilic in situ formed dicationic palladium species. Isomerisation of the diene and over-oxidation of the substrate could be nearly suppressed by suitable reaction control, which has a positive effect on selectivity. The utilization of molecular oxygen as a green oxidant and environmentally benign iron(iii) salts as co-catalysts was successfully applied. This reaction strategy is promising to overcome the low overall reactivity of internal olefins in Wacker type oxidations. In addition, larger scale experiments showed further potential for industrial application.
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