Selective isomerization-carbonylation of a terpene trisubstituted double bond

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2014
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Grau, Etienne
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urn:nbn:de:bsz:352-0-258649
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10.1039/C4GC01233J
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Green Chemistry ; 16 (2014), 10. - pp. 4541-4545. - ISSN 1463-9262. - eISSN 1463-9270
Abstract
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].
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540 Chemistry
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ISO 690BUSCH, Hanna, Florian STEMPFLE, Sandra K. HESS, Etienne GRAU, Stefan MECKING, 2014. Selective isomerization-carbonylation of a terpene trisubstituted double bond. In: Green Chemistry. 16(10), pp. 4541-4545. ISSN 1463-9262. eISSN 1463-9270. Available under: doi: 10.1039/C4GC01233J
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@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}
}
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    <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>
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