Selective isomerization-carbonylation of a terpene trisubstituted double bond

Busch, Hanna; Stempfle, Florian; Hess, Sandra K.; Grau, Etienne; Mecking, Stefan

Selective isomerization-carbonylation of a terpene trisubstituted double bond

Dateien

Busch_0-258649.pdfGröße: 287.37 KBDownloads: 631

Datum

2014

Autor:innen

Grau, Etienne

Open Access-Veröffentlichung

Open Access Green

Sammlungen

Chemie

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

Green Chemistry. 2014, 16(10), pp. 4541-4545. ISSN 1463-9262. eISSN 1463-9270. Available under: doi: 10.1039/C4GC01233J

Zusammenfassung

Selective catalytic carbonylation of the trisubstituted double bond of citronellic acid is enabled via an isomerization–functionalization approach. Alkoxycarbonylation with [{1,2-(^tBu₂PCH₂)₂C₆H₄}Pd(OTf)₂] as a catalyst precursor occurs with >97% selectivity for the terminal diester dimethyl-3,7-dimethylnonane-dioate. This prevails much over the typical cationic methoxyaddition. The reactive primary carboxy group formed allows for e.g. the preparation of the high molecular weight novel polyester poly[3,7-dimethylnonanediyl-3,7-dimethylnonanedioate].

Fachgebiet (DDC)

540 Chemie

Zitieren

ISO 690

BUSCH, Hanna, Florian STEMPFLE, Sandra K. HESS, Etienne GRAU, Stefan MECKING, 2014. Selective isomerization-carbonylation of a terpene trisubstituted double bond. In: Green Chemistry. 2014, 16(10), pp. 4541-4545. ISSN 1463-9262. eISSN 1463-9270. Available under: doi: 10.1039/C4GC01233J

BibTex

@article{Busch2014Selec-29312,
  year={2014},
  doi={10.1039/C4GC01233J},
  title={Selective isomerization-carbonylation of a terpene trisubstituted double bond},
  number={10},
  volume={16},
  issn={1463-9262},
  journal={Green Chemistry},
  pages={4541--4545},
  author={Busch, Hanna and Stempfle, Florian and Hess, Sandra K. and Grau, Etienne and Mecking, Stefan}
}

RDF

<rdf:RDF
    xmlns:dcterms="http://purl.org/dc/terms/"
    xmlns:dc="http://purl.org/dc/elements/1.1/"
    xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#"
    xmlns:bibo="http://purl.org/ontology/bibo/"
    xmlns:dspace="http://digital-repositories.org/ontologies/dspace/0.1.0#"
    xmlns:foaf="http://xmlns.com/foaf/0.1/"
    xmlns:void="http://rdfs.org/ns/void#"
    xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > 
  <rdf:Description rdf:about="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29312">
    <dc:contributor>Busch, Hanna</dc:contributor>
    <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/29312/1/Busch_0-258649.pdf"/>
    <dc:creator>Busch, Hanna</dc:creator>
    <dc:contributor>Stempfle, Florian</dc:contributor>
    <dcterms:rights rdf:resource="https://rightsstatements.org/page/InC/1.0/"/>
    <dc:contributor>Mecking, Stefan</dc:contributor>
    <dcterms:abstract xml:lang="eng">Selective catalytic carbonylation of the trisubstituted double bond of citronellic acid is enabled via an isomerization–functionalization approach. Alkoxycarbonylation with [{1,2-(&lt;sup&gt;t&lt;/sup&gt;Bu&lt;sub&gt;2&lt;/sub&gt;PCH&lt;sub&gt;2&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;C&lt;sub&gt;6&lt;/sub&gt;H&lt;sub&gt;4&lt;/sub&gt;}Pd(OTf)&lt;sub&gt;2&lt;/sub&gt;] as a catalyst precursor occurs with &gt;97% selectivity for the terminal diester dimethyl-3,7-dimethylnonane-dioate. This prevails much over the typical cationic methoxyaddition. The reactive primary carboxy group formed allows for e.g. the preparation of the high molecular weight novel polyester poly[3,7-dimethylnonanediyl-3,7-dimethylnonanedioate].</dcterms:abstract>
    <dc:contributor>Hess, Sandra K.</dc:contributor>
    <foaf:homepage rdf:resource="http://localhost:8080/"/>
    <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/29312/1/Busch_0-258649.pdf"/>
    <dc:creator>Mecking, Stefan</dc:creator>
    <dc:creator>Stempfle, Florian</dc:creator>
    <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2014-11-26T10:01:13Z</dc:date>
    <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/29312"/>
    <dc:rights>terms-of-use</dc:rights>
    <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2014-11-26T10:01:13Z</dcterms:available>
    <dc:language>eng</dc:language>
    <dc:contributor>Grau, Etienne</dc:contributor>
    <dc:creator>Grau, Etienne</dc:creator>
    <dcterms:issued>2014</dcterms:issued>
    <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dc:creator>Hess, Sandra K.</dc:creator>
    <dcterms:title>Selective isomerization-carbonylation of a terpene trisubstituted double bond</dcterms:title>
  </rdf:Description>
</rdf:RDF>

Universitätsbibliographie

Ja