Selective Wacker type oxidation of a macrocyclic diene to the corresponding monounsaturated ketone used as fragrance

dc.bibliographicCitation.firstPage27865eng
dc.bibliographicCitation.issue48eng
dc.bibliographicCitation.journalTitleRSC Advanceseng
dc.bibliographicCitation.lastPage27873eng
dc.bibliographicCitation.volume9eng
dc.contributor.authorBrunzel, Tom
dc.contributor.authorHeppekausen, Johannes
dc.contributor.authorPanten, Johannes
dc.contributor.authorKöckritz, Angela
dc.date.accessioned2022-05-10T09:51:30Z
dc.date.available2022-05-10T09:51:30Z
dc.date.issued2019
dc.description.abstractA 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. This journal is © 2019 The Royal Society of Chemistry.eng
dc.description.versionpublishedVersioneng
dc.identifier.urihttps://oa.tib.eu/renate/handle/123456789/8926
dc.identifier.urihttps://doi.org/10.34657/7964
dc.language.isoengeng
dc.publisherCambridge : RSCeng
dc.relation.doihttps://doi.org/10.1039/c9ra04971a
dc.relation.essn2046-2069
dc.rights.licenseCC BY-NC 3.0 Unportedeng
dc.rights.urihttps://creativecommons.org/licenses/by-nc/3.0/eng
dc.subject.ddc540eng
dc.subject.otherIron compoundseng
dc.subject.otherKetoneseng
dc.subject.otherMolecular oxygeneng
dc.subject.otherOlefinseng
dc.subject.otherEnvironmentally benigneng
dc.subject.otherIsomeric mixtureseng
dc.subject.otherOveroxidationseng
dc.subject.otherPalladium specieseng
dc.subject.otherReaction controleng
dc.subject.otherReaction strategieseng
dc.subject.otherSelective reactionseng
dc.subject.otherWacker-Type oxidationeng
dc.subject.otherOxidationeng
dc.titleSelective Wacker type oxidation of a macrocyclic diene to the corresponding monounsaturated ketone used as fragranceeng
dc.typeArticleeng
dc.typeTexteng
tib.accessRightsopenAccesseng
wgl.contributorLIKATeng
wgl.subjectChemieeng
wgl.typeZeitschriftenartikeleng
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